Thiosemicarbazide, 1, 3, 4-thiadiazole, antibacterial activity by ijsidonlineinfo

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									                                 Arvind K Singh et al., IJSID, 2011, 1 (3), 353-361


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                        International Journal of Science Innovations and Discoveries                   An International peer
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Research Article                                                      Available online through www.ijsidonline.info
  SYNTHESIS, CHARACTERIZATION AND ANTIBACTERIAL ACTIVITY OF 1, 3, 4-THIADIAZOLE DERIVATIVES
                             Arvind k. singh*, R.Parthsarthy, Kshitiz jyoti, Geeta mishra


   *kamla Nehru institute of management and technology (faculty of pharmacy), Sultanpur, Uttar Pradesh, India,
                             *National institute of medical sciences, Jaipur, Rajasthan, India.


                                                                         ABSTRACT
Received: 13.09.2011                        2,5-Disubstituted 1,3,4-thiadiazoles show various pharmacological
Modified: 09.10.2011                activities and have been synthesized from different compounds .2,5

Published: 29.12.2011               Disubstituted 1,3,4- thiadiazole is popularly known for its antibacterial,
                                    antinflammatory and antihypertension activities etc.It is known that the
*Corresponding Author
                                    synthesis of heterocyclic compounds tend to contain various types of
                                    structure in molecules . The formation of ring system involves the
                                    condensation process Synthesis of derivatives of 1,3,4- thiadiazole from
                                    different acids . All the newly synthesized compound have been
                                    characterized by the IR, 1H NMR, MASS Spectral data by structural
                                    elucidation & all newly synthesized compounds were evaluated by the
                                    antimicrobial activity by disc diffusion methods & anti inflammatory
                                                 INTRODUCTION
                                    method by carreageenan rat paw edema method.
Name:
Arvind. K. Singh
Place:                              Key word: Thiosemicarbazide, 1, 3, 4-thiadiazole, antibacterial activity.
Sultanpur Uttar Pradesh, India
E-mail:                                             INTRODUCTION
adi_arv26@rediffmail.com




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                                                 INTRODUCTION
        Mostly five membered aromatic system having three heteroatom’s at symmetrical position have been
studied because of their physiological properties1-2. It is also well established that various derivatives of 1,3,4-
thiadiazole exhibit broad spectrum of pharmacological properties such as antibacterial and antifungal activities.3
1,3,4- thiadiazole showed antibacterial properties similar to those of well known sulfonamide drugs4. prompted by
their finding and in continuation of our efforts in synthesizing various condensed bridge pharmaceutically active
groups 5. During recent years there has been intense investigation of different classes of thiadiazole compounds,
many of which known to possess interesting biological properties such as antimicrobial, antituberculosis, anti-
inflammatory, anticonvulsants, antihypertensive, antioxidant, anticancer and antifungal activity6.
                                                 EXPERIMENTAL
        All chemicals were supplied by (Merck & S.D.fine chemicals Lucknow India). Meltingpoint(m.p) was
determined by open capillary tube method. Purification of the compounds was checked by column
chromatography & silica gel-G(60-120mess) & silica gel GF254 (4:1) for preparation of the TLC plates and used
the solvent system 5% ethyl acetate in pet. Ether & spots were seen under iodine vapours & UV light chamber. IR
spectra were obtained on a Perkin-Elmer 1720 FT-IR-Spectrometer (KBr-soln/pellets). 1HNMR spectra were noted
an Brucker Ac-400 MHz spectrometer using TMS as internal standard in DMSO/CDCl3 & mass spectra (m/z %)
recorded by VG ZAB-HS (FAB) instrument.
General procedure for the 1,3,4-thiadiazole derivatives:
        Taken the molar concentration (1:1) of aromatic acid & Thionyl chloride in RBF & shake properly and kept
the solution for refluxing for 3 to 4 hour at 600C with CaCl2 guard tube & then get product that was the aromatic
acid chloride &. added to (0.01 mole) thiosemicarbazide was mixed properly & added the excess benzene as the
solvent & shake properly chemical in Round bottom flask & refluxed for 3 to 6 hour at 600C. Then the product was
washed with NaHCO3 & recrystalized with ethanol. Checked the TLC for proper finding the solvent chloroform and
ethyl- acetate (8:6).
Characterization of compounds (Ia-Ig:)
        Compound Ia:[N-(5-phenyl-[1,3,4] thiadiazole-2-yl)-benzamide] :IR Data (KBr cm-1)):       680.4 (thiadiazole),
3421 (NH), 1623 (C=O).1HNMR Data( DMSO-d6,δ,ppm): 8.76 (s, 1H, J= 7.633), 7.77 (d,3H,7.623), 7.6 (5Hm,7.61).MASS
Data m/z (%): C15H11N3SO, calculated: C=64.05, H=3.91, N=14.94, found: C=63.11, H=3.85, N=14.72%).
Compound-Ib:[3-chloro-N-[5-(3-chloro-phenyl)-[1,3,4]      thiadiazole-2-yl]-benzamide]     :IR   (KBr   cm-1):   673.6
(thiadiazole), 3333.7 (NH), 1623.8 (C=O). 1HNMR (DMSO): 8.4(1H, s, J=7.73), 7.9(4Hx2, 7.709).MASS Data m/z: C15H9
Cl2N3SO, calculated: C=51.44, H=2.59, N=12.00, found: C=51.85, H=2.59, N=12.10%).
Compound-Ic:[4-chloro-N-[5-(4-chloro-phenyl)-[1,3,4]thiadiazole-2-yl]-benzamide]         :IR     (KBr   cm-1)    673.6
(thiadiazole), 333.7 (NH), 1623.8 (C=O).1HNMR (DMSO): 8.4(1H, s, J=7.73), 7.9(4Hx2, 7.709).MASS Data m/z:
C15H9Cl2N3SO, calculated: C=51.44, H=2.59, N=12.00, found: C=51.85, H=2.59, N=12.10%).

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Compound-Id:[4-Nitro      -N-[5-(2-Nitro-phenyl)-[1,3,4]     thiadiazole-2-yl]-benzamide]:IR   (KBr   cm-1)      657.7
(thiadiazole), 3404.2 (NH), 1628.8 (C=O).1H NMR Data ( DMSO-d6,δ,ppm): 8.7(1H, s, NH), 8.1(5x2H, m,aromatic-
H).MASS Data m/z (%): C15H9N5SO5: Calculated: C=48.52, H=2.44, N=18.86%), found:C=48.12, H=2.40, N=18.71%).
General procedure for the compounds and Characterization :(IIa-IId)
Compound IIa: 2-amino-5-phenyl-1, 3, 4-thiadiazole:
        Benzaldehyde (3gm, 0.1M) is dissolved in warm alcohol (42.4ml) and thiosemicarbazide (3gm, 0.1M) is
dissolved in warm water (49.45 ml) separately and were mixed both solutions slowly with continuous stirring.
Then cool the mixture it produces the product immediately. This was filtered with suction and dried. The product
was recrystallized from 50% ethanol to Found compound (I).Compound (I) Thiosemicarbazone) (2gm, 0.05M) was
suspended in (67ml) warm water. FeCl3 (4.436gm, 0.15M) was dissolved in (54.7 ml) water quantitatively, and
                                                                                                ̊
added to Compound (I) suspension slowly with constant stirring. The mixture was heated at 80-90 C for 45 min.
This solution was filtered hot and then added the citric acid (4.74gm, o.11M) and Sodium citrate (3.3gm, 0.05M)
with continuous stirring . The resulting mixture is neutralized with aq. Ammonia (10%). The mixture was filtered
with suction, dried and recrystallized with 50% alcohol to produce the compound (IIa). . Benzene: ethyl acetate:
ethanol (4:2:1) was used as mobile phase. The spots were visualized by exposure to iodine vapours.IR: cm-1 3403
(NH), 1514 (C=N), 1057 (N-N), 686 (C-S).1HNMR: (DMSO-d6, δ, ppm); 7.77-7.72(2H, d, NH2), 7.45-7.41(4H, m, Ar-
H) MASS: (m/2 %) Anal. Calculated for C8H7N3S: C, 53.58; H, 3.90; N, 23.44; S, 17.86. Found C, 53.91; H, 3.93; N,
23.58; S, 17.97. %.
Compound: - 2-amino-5-(4-methoxyphenyl)-1, 3, 4-thiadiazole
        Anisaldehyde (3gm, 0.1M) is dissolved in warm alcohol (42.4ml) and thiosemicarbazide (3gm, 0.1M) is
dissolved in warm water (49.45 ml) separately and were mixed both solutions slowly with continuous stirring.
Then cool the mixture it produces the product immediately. This was filtered with suction and dried. The product
was recrystallized from 50% ethanol to Found compound (I).Compound (I) Thiosemicarbazone) (2gm, 0.05M) was
suspended in (67ml) warm water. FeCl3 (4.436gm, 0.15M) was dissolved in (54.7 ml) water quantitatively, and
                                                                                                ̊
added to Compound (I) suspension slowly with constant stirring. The mixture was heated at 80-90 C for 45 min.
This solution was filtered hot and then added the citric acid (4.74gm, o.11M) and Sodium citrate (3.3gm, 0.05M)
with continuous stirring . The resulting mixture is neutralized with aq. Ammonia (10%). The mixture was filtered
with suction, dried and recrystallized with 50% alcohol to produce the compound (IIb). . Benzene: ethyl acetate:
ethanol (4:2:1) was used as mobile phase. The spots were visualized by exposure to iodine vapours.IR: (KBr cm-1
)3410 (NH), 1512 (C=N), 1022 (N-N), 621 (C-S). 1HNMR: (DMSO-d6, δ, ppm); 8.01(2H, s, NH2), 7.79-7.77(3H, d,
OCH3), 6.97-6.89(4H, m, Ar-H). MASS: (m/2 %) Anal. Calculated for C9H9N2OS: C, 51.60; H, 4.30; N, 20.08; O, 7.65;
S, 15.30%. Found C, 51.90; H, 4.32; N, 20.18; O, 7.68; S, 15.37. %.



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Compound IIc: - 2-amino-5-(3-nitrophenyl)-1, 3, 4-thiadiazole
        3-nitrobenzaldehyde (3gm, 0.1M) is dissolved in warm alcohol (42.4ml) and thiosemicarbazide (3gm,
0.1M) is dissolved in warm water (49.45 ml) separately and were mixed both solutions slowly with continuous
stirring. Then cool the mixture it produces the product immediately. This was filtered with suction and dried. The
product was recrystallized from 50% ethanol to Found compound (I).Compound (I) Thiosemicarbazone) (2gm,
0.05M) was suspended in (67ml) warm water. FeCl3 (4.436gm, 0.15M) was dissolved in (54.7 ml) water
quantitatively, and added to Compound (I) suspension slowly with constant stirring. The mixture was heated at 80-
   ̊
90 C for 45 min. This solution was filtered hot and then added the citric acid (4.74gm, o.11M) and Sodium citrate
(3.3gm, 0.05M) with continuous stirring . The resulting mixture is neutralized with aq. Ammonia (10%). The
mixture was filtered with suction, dried and recrystallized with 50% alcohol to produce the compound (IIc). .
Benzene: ethyl acetate: ethanol (4:2:1) was used as mobile phase. The spots were visualized by exposure to iodine
vapours. IR:(KBr cm-1) 3406 (NH), 1525 (C=N), 1402 (NO2), 1053 (N-N), 680 (C-S). 1HNMR: (DMSO-d6, δ, ppm);
8.62(2H, s, NH) 2.65-2.55(4H, m, Ar-H). MASS: (m/2 %) Anal. Calculated for C8H6N4O2S: C, 42.83; H, 2.67; N, 24.98;
O, 14.27; S,14.27%. Found C, 43.03; H, 2.68; N, 25.10; O, 14.34; S, 14.34. %.
Compound IId: - 2-amino-5-(6-hydroxyphenyl)-1, 3, 4-thiadiazole:
        Salicylaldehyde (3gm, 0.1M) is dissolved in warm alcohol (42.4ml) and thiosemicarbazide (3gm, 0.1M) is
dissolved in warm water (49.45 ml) separately and were mixed both solutions slowly with continuous stirring.
Then cool the mixture it produces the product immediately. This was filtered with suction and dried. The product
was recrystallized from 50% ethanol to Found compound (I).Compound (I) Thiosemicarbazone) (2gm, 0.05M) was
suspended in (67ml) warm water. FeCl3 (4.436gm, 0.15M) was dissolved in (54.7 ml) water quantitatively, and
                                                                                                ̊
added to Compound (I) suspension slowly with constant stirring. The mixture was heated at 80-90 C for 45 min.
This solution was filtered hot and then added the citric acid (4.74gm, o.11M) and Sodium citrate (3.3gm, 0.05M)
with continuous stirring . The resulting mixture is neutralized with aq. Ammonia (10%). The mixture was filtered
with suction, dried and recrystallized with 50% alcohol to produce the compound (IId) . Benzene: ethyl acetate:
ethanol (4:2:1) was used as mobile phase. The spots were visualized by exposure to iodine vapours. IR:(KBr cm-1 )
3396 (NH), 3139 (OH), 1482 (C=N), 105 (N-N), 705 (C-S). 1HNMR: (DMSO-d6, δ, ppm); 7.86(1H, s, OH), 7.23-
7.34(4H, m, Ar-H), 6.98-6.86(2H, d, NH2). MASS: (m/2 %) Anal. Calculated for C8H7N3OS: C, 49.07; H, 3.60; N,
21.52; O, 8.19; S, 16.39%. Found C, 49.46; H, 3.60; N, 21.64; O, 8.24; S, 16.48. %.
Antibacterial Activity:7
        The synthesized compounds were evaluated for their antimicrobial activity against Staphylococcus aureus
(gram+ve), B.Subtilis (gram+ve), P.aeuroginosa (gram-ve) and Escherichia coli (gram-ve) by cup plate agar diffusion
method by measuring the inhibition zone in mm. Concentration (10µg/disc) was used as a standard drug for
antibacterial activity. The compounds were screened for antibacterial activity against E.coli, S.aureus, P.
aeuroginosa, in nutrient agar medium. These sterilized agar media were poured into petri-dishes and allowed to

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solidify. On the surface of the media microbial suspensions were spread with the help of sterilized triangular loop.
A stainless steel cylinder of 8 mm diameter (pre-sterilized) was used to bore cavities. All the synthesized
compounds (5µg/disc) were placed serially in the cavities with the help of micropipette and allowed to diffuse for
1.0 hr. DMF was used as a solvent for all the compounds, and as a control. These plates were incubated at 370C for
34 hrs for antibacterial activity. The zone of inhibition observed around the cups after incubation was measured
and percent inhibition of the compounds was calculated.
                                       Table I- Spectral data of compound (Ia-Id and IIa-IId)
S.N.   Code          MolecularFormula                                                Analytical data

                                               IR (cm1)                1HNMR(DMSO,d6,δ,ppm)                     MASS

                                                                                                                (Calculated)             (found)

1      Ia            C15H11N3SO              680.4(thiadiazole),3421   δ8.76        (s,      1H,           J=   C=64.05,       H=3.91,   C=63.11, H=3.85,
                                             (NH),1623(C=O)            7.633),7.77(d,3H,7.623),7.6              N=14.94,                 N=14.72%)
                                                                       (5Hm,7.61)


2      Ib            C15H9 Cl2N3SO,          673.6(thiadiazole),3333   8.4(1H,s,J=7.73),7.9(4Hx2, 7.709)        C=51.44, H=2.59,         C=51.85, H=2.59,
                                             .7(NH),1623.8(C=O)                                                 N=12.00                  N=12.10%)



3      Ic            C15H9 Cl2N3SO           3333.7(NH),               8.4(1H,S,J=7.73),7.9(4Hx2, 7.709)        C=51.44, H=2.59,         C=51.85,H=2.59,
                                             1623.8(C=O),673.6(thia                                             N=12.00                  N=12.10%)
                                             diazole)


4      Id            C15H9N5SO5              657.7                     8.7(1H,S,NH), 8.1(5x2H,m, aromatic       C=48.52, H=2.44,         C=48.12, H=2.40,
                                             (thiadiazole),3404.2(NH   H)                                       N=18.86%),               N=18.71%)
                                             ),1628.8(C=O)


5      IIa           C8H7N3S                 3403(NH),1514(C=N),1      7.77-7.72(2H,d,NH2),7.45-                C,53.58% H,3.90%         C,53.91% H,3.93%
                                             057(N-N),686(C-S)         7.41(4H,m,Ar-H)                          N,23.44%S,17.86%         N,23.58% S,17.97%

6      IIb           C9H9N3OS                3410(NH),1512(C=N),1      8.01(2H,s,NH2),7.797.77(3H,d,OCH3        C,51.60% H,4.30%         C,51.90% H,4.32%
                                             022(N-N),621(C-S)         ),6.97-6.89(4H,m,Ar-H)                   N,20.08%O,7.65%S,1       N,20.18%O,7.68%
                                                                                                                5.30%                    S,15.37%



7      IIc           C8H6N4O2S               3406(NH),1525(C=N),1      8.62(2H,s,NH),2.65-2.55(4H,m,Ar-         C,42.83% H,2.67%         C,43.03% H,2.68%
                                             402(NO2),1053(N-          H)                                       N,24.98% O,14.27%        N,25.10%O,14.34%
                                             N),680(C-S)                                                        S,14.27%                 S,14.34%

8      IId           C8H7N3OS                3396(NH),3139(OH),14      7.86(1H,s,OH),7.23-7.34(4H,m,Ar-         C,49.07% H,3.60%         C,49.46% H,3.60%
                                             82(C=N),105(N-            H),6.98-6.86(2H,d,NH2)                   N,21.52%O,8.19%S,1       N,21.64%O,8.24%
                                             N),705(C-S)                                                        6.39%                    S,16.48%




                                                      RESULT & DISCUSSION
Chemistry:
            All compounds were structurally characterized by using IR, H1-NMR and MASS analysis. The IR absorption
band around 686cm-1, 3403cm-1, 1514 cm-1, 1057 cm-1, could be attributed to the –C-S-, NH, C=N, N-N,Functional
group. The 1HNMR spectra 7.77-7.72(2H, d, NH2), 7.45-7.41(4H, M, Ar-H) showed the presence of singlet, doublet,

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and multiplets peaks which represented the presence of aromatic, amine, and hydroxyl protons respectively. Mass
spectra (m/z %) Anal. Calcd for C8H7N3S: C,53.58; H, 3.90; N, 23.44; S, 17.86. Found C, 53.91; H, 3.93; N, 23.58; S,
17.97. % showed the calculated and founded value of the compound.
Antibacterial activity:
           Synthesis and screening of 2-amine-5-phenyl-1,3,4-thiadiazole(IIa), 2-amine-5-(4-nitrophenyl)-1,3,4-
thiadiazole(IIb), 2-amine-5-(4-methoxyphenyl)-1,3,4-thiadiazole(IIc) and 2-amino-5-(5-hydroxy phenyl)-1,3,4-
thiadiazole(IId) were tested for the antibacterial activity against following bacteria. a) i) S. aureus, ii) B.subtilis
(gram+ve); b) iii) E. coli, iv) pseudomonas (gram –ve). The test compounds IIa, IIb, IIc, IId                       showed good
antibacterial activity against Bacillus subtilis (gram +ve) and P.aeuroginosa at lower and higher concentrations and
compounds IIa, IIb showed promising antibacterial activity against Staphylococci(gram+ve) and E. Coli (gram –ve)
at higher and lower concentrations. Only compound IIc has shown moderate antibacterial activity against
P.aeroginosa (gram -ve) where as the test compounds IIb, and IId showed moderate antibacterial activity compared
to Ciprofloxacine against pseudomonas (gram–ve).
                                Table: II -Physical properties of compounds (Ia-Id and IIa-IId)
Compounds         M. formula        M.P.   Yield             Solvent system                  R.f value   M.wt.         Colour
   1a             C15H11N3SO        83     70.43   Chloroform ethyl- acetate (8:6),            0.804     281         Pale yellow
   1b             C15H9N3SOCl       87     67.31     Chloroform ethyl- acetate (8:6),          0.694     349        Lemon yellow
                       2
     1c           C15H9N3SOCl       87     72.40     Chloroform ethyl- acetate (8:6),            0.706    349        Pale yellow
                       2
     1d            C15H9N5SO3       114    66.24      Chloroform ethyl- acetate (8:6),           0.634    371          Brick red
     IIa            C8H7N3S         225     64     Benzene: ethyl acetate:                       0.63    177.22       Slight pink
                                                   ethanol(4:2:1)
     IIb           C9H9N3OS         220    67.3    Benzene: ethyl acetate:ethanol(4:2:1)         0.58    207.25        Greenish
                                                                                                                        brown
     IIc           C8H6N4O2S        257    77.7    Benzene: ethyl acetate:ethanol(4:2:1)         0.71    222.22      Light Yellow
     IId           C8H7N3OS         110    81.8    Benzene: ethyl acetate:ethanol(4:2:1)         0.54    193.22         Black
Scheme: 1
                                              Reflux       3-4 hr
                 R - COOH       +    SOCl2                                    R- COCl                    1st step

                                                                                +
                                                                              NH2NHCSNH2


                                                                                    Reflux

                                                                                    3 - 6 hr




                                                                                                         2nd step
                                                                            N       N



                                                                                S
                                                            R-CONH                           R

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                             Arvind K Singh et al., IJSID, 2011, 1 (3), 353-361
Scheme: 2
                         O
                                                                           S
                    R
                                      +              H 2N             NH        NH2




                                              H OH                                    S te p - 1
                                                     S

                              N         NH                  NH2
                   R
                                        (I)


                                                      2+                              S te p - 2
                                                 Fe


                                  N          N

                         R                           NH2
                                      S

                                      (II)



     Compounds No                                R                             Compounds No        R

            1a                                                                        IIa




            1b                                              Cl                        IIb




            1c                                                                        IIc
                                                                 Cl


            1d                                                                        IId

                                                            NO2




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                            Table: III Antibacterial activity of compounds (Ia-Id to IIa-IId)
                                             Zone of inhibition in mm.
Compounds        S.aures               B.subtilis                  E.coli                     P.aeruginosa
                (zone of      %        (zone of         %         (zone of          %            (zone of         %
                inhibitio   inhibi inhibition in inhibiti inhibition in inhibition            inhibition in   inhibition
                n in mm)     tion        mm)           on           mm)                            mm)
      Ia            12        48          20          76.84          14          49.98              18           72
      Ib            15        60          18          69.12          23          53.55              12           48
      Ic            16        64          15          57.6           18          64.26              16           64
      Id            18        72          21          80.64          16          57.12              21           56
     IIa            11        44          17          65.38          15          53.57              16           64
     IIb            12        48          18          69.23          14          50.01              17           68
     IIc            15        60          20          76.92          15          53.57              18           72
     IId            14        56          17          65.38          16          57.14              17           68
Ciprofloxacin       25       100          26           100           28            100              25           100

                                                    CONCLUSION
         In conclusion, simple and convenient methods for synthesis of the new substituted 1, 3, 4-thiadiazole
derivatives, and reported the antibacterial and anti-inflammatory studies of these derivatives. The total of eight
derivatives were synthesized and screened for their antibacterial activity against S. aureus, B. subtilis, (gram+ve)
and E. coli, P. aeuroginosa (gram-ve) bacteria. The MIC of all compounds was determined by observing the zone of
inhibition formed around the cup after 24 hr of incubation for antibacterial activity. Compounds were found to
have moderate antibacterial activity. These substituted thiadiazole derivatives can be selected for further studies
since it contains Chloro, methoxy, hydroxy, nitro group’s substitution, it showed significant anti-inflammatory
activity compared to Ibuprofen respectively. According to this study, we could point out that substituted 1, 3, 4-
thiadiazole derivatives played a very important role as anti-inflammatory and antibacterial agents. These
observations may provide some predictions in order to design further promising thiadiazole compounds.
                                               ACKNOWLEDGEMENT
       I am thankful to my sincere project guide “Dr R.Parthasarthy” (Director of KNIMT faculty of pharmacy) for
provide proper guidance towards our project work & thankful to CDRI, Lucknow for spectral analysis of
compounds.
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    3. HUI XP, CHU CH, ZANGZU, WANG Q and ZHANG Q (2002). Synthesis and antibacterial activity of 1,3,4-
       Thiadiazole derivatives of 5-amino,2-hydroxybenzoic acid. Indian Journal of. Chemistry., 41B: 2176.


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