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Der Pharma Chemica, 2011, 3(1): 523-537 (http://derpharmachemica.com/archive.html)

ISSN 0975-413X CODEN (USA): PCHHAX

Thiazole: A valuable insight into recent advances, synthesis and biological activities

Amrita A Zagade*, Senthilkumar G. P. Bharathi College of Pharmacy. Bharathinagara, Mandya, Karnataka- 571422 ____________________________________________________________________________ ABSTRACT 2-Aminothiazoles and their derivatives have long been used as precursors for the synthesis of biologically active molecules. Because of the wide spectrum of activity shown by the thiazole moiety, numerous thiazoles substituted with different groups at various positions have been prepared. Despite this importance, 2-aminothiazoles have not been previously reviewed. In recent years, several new methods for the preparation of 2-aminothiazole derivatives and reactions have been reported, including waste-free techniques. Thiazoles displayed the broad range of biological activities and found in many potent biologically active. Molecules such as Sulfathiazole (antimicrobial drug), Ritonavir (antiretroviral drug), Abafungin (antifungal drug).So far, the modifications of the thiazole ring have proven highly effective and improved potency and lesser toxicity. The present review highlights the recently synthesized thiazoles possessing important biological activities. Keywords: Thiazoles, Antibacterial, Anticancer. ____________________________________________________________________________ INTRODUCTION Thiazolederivatives a wide range of biological activities such as cardiotonic1, fungicidal, sedative, anesthetic, bactericidal and anti-inflamatory. The synthesis of thiazole derivatives is important of their wide range of pharmaceutical and biological properties. The most straight forward procedure reported by Hantzch in 1887 involves condensation of haloketones and thiourea or thioamides in refluxing alcohol. this method is long reaction time (24-25 h), harsh reaction conditions. Thiazole derivatives are known to exhibit biological activities such as bacteriostatic, fungistatic, anti-thrombotic, anti-inflammatory, anesthetic, antihypertensive and sedative. Some thiazole derivatives particularly 2-amino-4-arylthiazoles have been shown to posses antitubercular activity[1,6,7,8]anti-microbial[9,10,11,12]. Acetophenones prepared by known methods were condensed with thiourein the presence of iodine to give 2-amino-4-arylthiazoles.

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________ Thiazoles containing N=C-S moiety has been employed as antipsychotic and anti-bacterial. Thiazoles derivatives particularly amino thiazoles play vital role in pharmaceutical practices. The substituted thiazoles compounds have number of charecteristics pharmacological features such as: 1. 2. 3. 4. Relative stability and ease of starting material. Built in biocidal unit. Enhanced lipid solubility with hydrophilicity. Easy metabolism of compounds.

It was reported that thiazoles showed anti-bacterial activity when substituted with m-phenyl sulphonamido group at its 4th position, presence of benzyl group at 2 position reveals that it is found to be biological activity. Chemistry: Thiazoles or 1,3-thiazole, is a clear to pale yellow flammable liquid with a pyridine like odour and the molecular formula C3H3NS . It is 5-membered ring, in which two of the vertices of the ring are nitrogen and sulphur and the other three carbon. Thiazoles are class of organic compounds related to azoles with the common thiazole functional group. Thiazoles are aromatic. Structure of Thiazole:

S N

Various laboratory methods exist for the the organic synthesis of thiazoles: 1. The Hantzschthiazole synthesis (1889) is a reaction between haloketones and thioamides 2. In an adaptation of the Robinson-Gabriel synthesis, a 2-acyl-amino-ketones reacts with phosphorus pentasulfide. 3. In the Cook-Heilborn synthesis, an -aminonitrile reacts with carbon disulphide. 4. Certain thiazoles can be accessed through application of Hertz reaction. Resonance of the thiazole: Thiazole is aromatic on the basis of delocalization of a lone pair of electrons from the sulfur atom completing the needed 6 electrons to satisfy Huckel's rule. The resonance forms are:

N S C

-

H N S

+

CH N S

+

-

N HC

-

N S

+

S

+

CH

-

Structure-Activity Relationship: 1.The 2-chloro derivatives shows moderate to good increases in anti-tubercular activity[4]. 2.These compounds exhibit very moderate activity against various gram positive and gram negative bacteria. The compounds with methyl substitution in the 5-position of the thiazole ring were found to be less active against M.tuberculosis than the compound with no substitution in

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________ the 5-position. The compounds with the methyl substituted benzyl group at the 2-position of the thiazole ring were found to be more active against tubercle bacilli than the compounds exhibiting a phenyl group at the 2-position[6]. 3.It was reported thiazoles exhibits wide spectrum of biological properties. It shows antibacterial activity when substituted with m-phenylsulponamido group at its 4-position. The presence of benzyl group at 2-position of the thiazole ring reveals of its biological activity[11]. 4.The marked inhibition in bacteria was observed in the compound, others have shown moderate and less activity. The potent derivatives that have highly electronegative part of sulfhydryl group, specifically these compounds are Schiff bases,probably due to their ability to increase the penetration in the bacterial cell. It may be noted that cyano group may not have any role in increase in activity. The optimization of sulfhydryl compound reveals loss of activity. The studies shows that the free amino group have open area for the further modifications. When the compounds were treated with the acid chlorides, it showed increase in anti-microbial activity[10]. 5.The different thiazole molecules when fused with pyrazole ringcontaining heterocycles presents anti-bacterial activity[12]. 6.The arylaminothiazoles were found to possess effective anti-bacterial and anti-inflammatory activity[18]. Synthesis: 1)Scheme-1 V E Bhingolikar et al[1], have synthesized 2-amino-4-aryl-5-arylsulfonyl thiazoles have been successfully carried out in one pot by condensing -aryl sulfonyl-4-substituted acetophenones with phenyl trimethyl ammonium tribromide and thiourea. The required -aryl sulfonyl-4substituted acetophenones have also been prepared by modified one pot method.

O O S O R R

1

S

+

PTT

+

H 2N

NH2

Acetonitrile

R

O R

1

N S NH2

S O

2)Scheme-2 O.V. Platonova et al[2], synthesised biheterocyclic thiazoles-aminooxadiazole, the potential biologically active compounds is developed. Regularities of transformations and physicochemical charecteristics of intermediates and final compounds are revealed.

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________

O

O

N

O O

NH2NHaq

O R1

O O Cl CH3

R1 N

S

R1 N

S

NH NH2 CH3

CH3

CH3

BrCN ROH, NaCO3

O R1 N CH3 S N N

NH2

3)Scheme-3 Patta S R et al[3], synthesized new series 5-[1-(4-(4-sustituted-pheenylamino)-meth-(z)ylidene]-thiazolidine-2,4-diones derivatives were synthesized. The structure of the synthesized compounds were confirmed on the basis of IR,H1NMR, etc. The compounds were screened for their antitubercular activity. Some of these compounds have shown promising anti tubercular activity.

O S ClCH2COOH

+

Water

NH S O CHO

H2N

NH2 Conc.HCl, 10 hr.

Cl

Reflux Piperidine Toulene

O S R NH O

(A1-A7)

DMF, Cu Powder K2CO3 RNH2

O S Cl O NH

NH

HO R= Cl H3C HOOC

F

OMe

O 2N

HOOC

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________

O Cl S

Br2

+

CH3

H 2N NH2

24 hr

Cl S 1

N NH2

COOH

CH

2 Cl

COOH CH

2 Cl

+

NH2

Cl O NH O

K 2 CrO

3

Dry Benzene

1

O N N

N S CH

2 ClNHR

Cl

RNH2 Dry Benzene Acetic anhydried

O N N

N S CH

2 Cl

Cl

R= C

6 H 4 Cl

4)Scheme-4 Andreani A et al[4], A number of selected imidazo[2,1-b]thiazoles entered the screening at the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) and one of these compounds, 2-chloro-6-phenylimidazo[2,1-b]thiazole, showed anti-tubercular activity. On this basis we planned the synthesis of new analogues bearing a substituted ring at the 6-position. The antitubercular activity of these compounds with the known analogues lacking the chlorine at the 2-position. 5-Nitroso--6-p-chlorophenylimidazo[2,1-b]thiazole showed potent antitubercular activity.

N S NH 2 Br

+

O

N R1 R S N R1

R

NANO 2 /AcOH

ON N Cl S N Cl

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________ 5)Scheme-5 Pattan S R et al[5] synthesised a new series of N-3[4-(4-chlorophenyl thiazole-2-yl)-2-amino methyl]quinazoline-4(3H)-one and their derivatives are synthesized. The structures of the title compounds are confirmed on the basis of IR and 1HNMR. The compounds are screened for their anti tubercular activity, using H37Rv strain on L J medium. All the compounds have showed moderate to promising anti tubercular activity. 6)Scheme-6 Manian A et al[6] have been prepared by the condensation of 3-o-chlorophenyl-5-methyl isoxazole-4-tubercularrbonyl chloride with various 2-substituted ­anilino/phenyl/benzyl-5substituted- 4-(p-aminophenyl)-thiazoles. These compounds exhibited invitro antitubercular activity against the H37Rv strain of M. tuberculosis.

Cl COCl N O CH3 H2N S N

+

Acetone/(C H5)3N 2

Cl

O

N O CH3

NH S

N R

1

R

7)Scheme-7 Sonawane S et al[7], synthesized several new 2-(2'-substituted ­arylidene-hydrazino-acetylamino)-4-phenyl-1,3-thiazoles and 2-[2'-{4"-substituted ­aryl-3"-chloro-2"-oxo-azetidine}acetyl-amino]-4-phenyl--1,3 ­thiazoles, have been synthesized from 2-(2'-hydrazino-acetyl)amino-4-phenyl-1,3-thiazole using 2-amino-4-phenyl thiazole as the starting material. All the synthesized products are evaluiated for the anti fungal activity against Aspergillusflavus, Fusariumoxisporium, and Trichodermavirideand anti bacterial activity against Bacillus substilis, Eschericha coli and Staphylococcus aureus.

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ClCOCH2Cl

N S NH2

N S NHCOCH

2 .Cl

N H 2N H 2H 2O

N S

3a-n C lC O C H 2 C l/TE A

Ar2CHO/CH3COOH

N NHCOCH

2 NHNHCHAr

S

NHCOCH

2 NHNHNH 2

N S NHCOCH

2 NHNH

CHAr

H 2O

4a-n

HCl

8)Scheme-8 Chang-Ling Liu et al[8], synthesized novel 2-methyl-4-trifluro methylthiazole-5-carboxamide derivatives were deaigned and synthesized utilizing ethyl 4, 4, 4- trifluroacetoacetate as a starting material. Subsequently, the biological activity of the compounds have some fungicidal and insecticidal activity but no herbicidal activity .

O O F3C O

a

O

b

N OC2H5 H3C S

4 c

CH3 OCH3 O

F3C OC2H5

3

Cl

N H3C S

CH3 NHR O

e

N H3C S

CH3 Cl O

d

N H3C S

CH3 OH O

5

2

6

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________ Biological Activities: 1) Anti-tubercular activity: Pattan R et al[3], synthesized new series 5-[1-(4-(4-sustituted-pheenylamino)-meth-(z)-ylidene]thiazolidine-2,4-diones derivatives were. The structure of the synthesized compounds were confirmed on the basis of IR,H1NMR, etc. The compounds were screened for their antitubercular activity. Some of these compounds have shown promising anti tubercular activity.

O N NH S

OH COCH

Aldo Andreani et al[4], A number of selected imidazo[2,1-b]thiazoles entered the screening at the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) and one of these compounds, 2-chloro-6-phenylimidazo[2,1-b]thiazole, showed anti-tubercular activity. On this basis we planned the synthesis of new analogues bearing a substituted ring at the 6-position. The antitubercular activity of these compounds with the known analogues lacking the chlorine at the 2-position. 5-Nitroso--6-p-chlorophenylimidazo[2,1-b]thiazole showed potent antitubercular activity.

ON N Cl S N Cl

Pattan S et al[5], A new series of N-3[4-(4-chlorophenyl thiazole-2-yl)-2-amino methyl]quinazoline-4(3H)-one and their derivatives are synthesized. The structures of the title compounds are confirmed on the basis of IR and 1HNMR. The compounds are screened fro their anti tubercular activity, using H37Rv strain on L J medium. All the compounds have showed moderate to promising anti tubercular activity.

O N N

N S CH 2 NH

Cl

OH O

OH

Manian et al[6], have been synthesized 2-substituted anilino/phenyl/benzyl/-5- substituted-4phenylamido-(3-o-chlorophenyl-5-methylisoxazolyl) thiazoles exhibited in vitro antitubercular activity against H37RV strain

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________

Cl CONH N O CH3 R S R1 N

R = H, R! = NHPh Pattan et al[9], have been synthesized and evaluated some of the new substituted phenyl thiazoles and derivatives for anti-tubercular activities where 2-amino-4-phenyl thiazole reacts with different substituted acetanilides and chloroacetylations of it or their substituted derivatives. The anti-tubercular screening was carried out by Lowenstain-Jensen egg medium with Mycobacterial tuberculosis of H37RV strain.

N S NH NH O

Mahendra S et al[10], have been synthesized a series of N-{4-[(4-amino-5-sulfanyl-4H-1,2,4triazol-3-yl)methyl]-1,3-thiazol-2-yl}-2-substituted-amide derivatives in good yield and characterized by IR, 1H NMR, mass spectral and elemental analysis. The compounds were evaluated for their preliminary in vitro antibacterial activity against Staphylococcus typhosa and then were screened for antitubercular activity against Staphylococcus aureus, E.coli, Pseudomonas aeruginosa and Salmonella typhosa and then were screened for antitubercular activity against Mycobacterium tuberculosis H37 Rv strain by broth micro dilutions assay method. The antibacterial data of the tested compounds indicated that most of the synthesized compounds showed better activity against bacteria compared to reference drugs. The in vitro tubercular activity reports of tested compounds against M. tuberculosis strain H37Rv showed moderate to better activity.

N N R S Ar

-

N N SCH2CONHCHC6H5 O

HN

2) Anti-microbial activity: Manian et al[6], have been synthesized 2-substituted anilino/phenyl/benzyl/-5- substituted-4phenylamido-(3-o-chlorophenyl-5-methylisoxazolyl) thiazoles exhibited in vitroantitubercular activity against H37RV strain and anti-microbial activity against S.aureus and E.coli.

Cl CONH N O CH3 R S R1 N

R = H, R! = NHPh

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________ Sonawne et al[7], have been synthesized 2-(2'-arylidine-hydrazino-acetyl amino)-4-phenyl-1,3thiazoles and 2-[2'-{4''-substuted-aryl-3''-chloro-2''-oxo-azetidine}-acetyl-amino]-4-phenyl-1,3thiazoles, and studied for their antifungal activity against Aspergilllusniger and antimicrobial activity against E.coli.

N S O NHCOCH 2NH N Cl CHAr

Ar =C6H5 Arulmoli et al[11],have been synthesized 2-substituted benyl-4-(p-phenylsulphonamido)-5unsubstituted/methyl thiazoles by treating 4-(-bromoacetyl/2-bromopropionyl)phenyl sulphonamides with appropriate 2-substituted phenyl-thio-acetamides in ethanol and evaluated for antibacterial activity against S.aureus, S.typhi and E.coli.

H2NO2S S

N R1 R

R = H, R1= Cl Sahu et al[12], have been synthesized 2-phenyl-3,5-diphenyl(substituted)-6-aryl- 3,3a,5,6tetrahydro-2H-pyrazolo(3,4-d) thiazoles and evaluated for its antibacterial activity against S.aureus, E.coli, Actinmomyces pyogene.

R1 N NH S N R Ar

Ar = 4-NO2-C6H5, R = 2-OH, R1 = 4-N(CH3)2 Shrivastava et al[13], have beensynthesized 2-amino benzthiazole derivative which are evaluated for their anti bacterial activity against E.coli, S.aureus and B.substilis.

N NHCOCH2NH S O H Ar N S H Ar

Ar =C6H5 Pattan et al[14], have been synthesised some new substituted mercaptothiazoles which are evaluated for their biological activity against S. aureus and A. niger.

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________

Cl S N CH2CONRR"

R = H, R" = C6H5 Ahluwalia V K et al[15], have been synthesized and studied anti microbial activity of Some 2Amino-4-aryl -5-chromannylazoles by the condensation of diazotised 6-amino-2,2-dimethyl-3,4dihydro-2H-1-benzopyran with different 2-amino-4-arylthiazoles . These compounds have been tested for their antifungal and antibacterial activities.

Cl

N Cl O N N S NH2

Pattan S R, N S et al[16], synthesized substituted amino thiazoles. The compound was tested in vitro for their anti-bacterial activity against two microorganisms viz. E.coli, S. aureus by disc diffusion method using Mullar-Hinton agar.

Cl N S NHCOCH2 OCOCH3

3) Anti-cancer activity: Reji et al[17], has synthesized and carried out cytotoxicity evaluation of 2-N, N-dimethyl amino5-indole-3-oylthiazole for anticancer marine alkaloid dendrodoine against NCI-H460, NCF7 and SF-268.

H N S O NMe2

N H

Q Zhao et al[18], have been synthesized, characterized and studied cytotoxicity regioselectivity of a series of novel glycosyl thiazol-2-imines from hydrolysis of thiazol-2(3H)-imine-linked glycoconjugates.

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________

R3 N R2 S N R4

PivO R2 = Ar R3 =

OPiv O R4 = ArCO OPiv

PivO

4) Cyclooxygenese inhibition activity: Venkateshwar et al[19], have been synthesized a series of 2- aminophenyl-5-phenyl-4-[3-oxo1,4-benzexazin-6-yl] thiazoles which are evaluated for their COX-2 inhibition activity.

O N R S

O

N

NH R1

R = H, R1 = C6H5 Unanget P C et al[20], have been synthesized and biological evaluation of 5-[[3,5-Bis(1,1dimethylethyl)-4-hydroxyphenyl]methylene]thiazoles derived from 2,6-di-tert-butylphenol, structure activity relationship was studied.

O

N S OH

Reddy G J et al[21], have been synthesized a series of methyl 5-[2-arylamino-4-(3-oxo-1,4benzoxazin-6-yl)thiazole acetates and 7H-[3-aryl-6-(3-oxo-1,4-benzoxazin-6-yl)-s-triazolo[3,4b][1,3,4]thiadiazine-7-yl]acetates as possible cox-2 inhibitors.

O CH2COCH3 S O N H N NHC6H5

5) Anti-viral activity: Pande A et al[22], have been synthesized some new 6-aryl-7-arylazo-4-phenyl-2H-thiazolo[3,2]-1,2,5-triazine-2-thiones and studied for their antiviral activity against Ranikhet disease virus.

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________

R C 6H 5 N N R1 N S N S N

R1 = 2-NO2, R = OCH3 6) Fungicidal activity: Chang li lu et al[8], synthesised novel 2-methyl-4-trifluromethyl-thiazole-5-carboxamide derivatives and evaluated for fungicidal and insecticidal activity.

N H3C S O CF3 NHR

Pattanaik J M et al[23], have been synthesized a series of 3-aryl-2-(4'-aryl thiazole-2'ylaminomethyl) quinazol-4(3H)-ones have been prepared by condensing 3-aryl-2chloromethylquinazol-4(3H)-oneswith 2-amino-4-substituted phenylthiazoles. The prepared compounds have been characterized by spectral data and antifungal activity was determined.

O

N N N HN S CH3

Hui Ling Lui et al[24],have been synthesized five derivatives of 2-imino-3-(4-arylthiazol-2yl)thiazolidin-4-ones and a series of their 5-arylidine derivatives and synthesized for antifungal activity against seven agricultural fungi.

Ar

-

N S N

O

S HN Ar=2,4-(Cl) 2C6H3

7) Antipsycotic activityTakeo Funakoshi et al[25], have been studied invitro and invivo pharmacological profile of 5-{2[4-(6-floro-1H-indole-3-yl)piperidine-1-yl]ethyl}-4-(4-fluorophenyl)thiazole-2-carboxylic acid amide,a novel typical antipsychotic drug. As an antipsychotic has a unique profile with affinity and occupancy for receptors.

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F

O N F H2N S N N H

CONCLUSION Thiazoles are easily available and offer countless modifications by numerous reaction modes in various positions due to their high reactivity. This has been comprehensively documented. Apart from the synthetic interest, the known and expected biological or medicinal activities of the numerous derivatives deserve particular mentions. REFERENCES [1] Bhingolikar V, Mahalle S, Bondage S, Mane R. Ind J Chem 2005; 44B: 2589-2593. [2] Platonova O, Volkova S, Malin S, Veretennikov E, Laskin B, Malin A. J App Chem 2008; 81(3):513-515. [3] Pattan S, Alagwadi K, Bhat A, Reddy V, Pattan J, Khade A, Bhat K. Ind Drugs 2007;45(7):532-535. [4] Andreni A, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M. Eur J Med Chem 2001;36: 743-746. [5] Pattan S, Reddy V, Manvi F, Desai B, Bhat A. Ind J Chem 2006; 45B: 1778-1781. [6] Manine A, Khadase B, Sengupta S. Ind Drugs 1994;31: 442-444. [7] Sonawne SK, Shrivastava SD, Shrivastava SK. Ind J Chem 2008; 47B: 633-636. [8] Chang Ling Liu, Zheng Ming Li, Bin Zhong. J Flu Chem 2004;125: 1287-1290. [9] Pattan SR, Bukitagar AA, Bhat KG, Pattan JS, Kittur BS, Khade AB. Ind Drugs 2007;44(9): 689-692. [10] Mahendra S, Murahari K, Gangadasu H, Tatikonda S, Kalyan C, Panchal D. Bio-org Med Chem 2007;15: 3997-4008. [11] Arulmoli T, Khadse BG. Ind J Pharm Sci 1994:192-195. [12] Sahu SK, Mishra SK, Mohanta NK, Panda PK, Azam AM. Ind J Pharm Sci 2007: 689-692. [13] Srivastva SD, Sen JP. Ind J Chem 2008; 47B:1583-1586. [14] Pattan S, Sirajunasia T, Pattan J. Ind J Chem 2004; 43B: 439-441. [15] Ahluwalia V, Raj S, Rishi S. Ind J Chem 1987; 26B: 287-289. [16] Pattan S, Dighe N, Nirmal S, Merekar A, Laware R, Shinde H, Musmade D. Asian J Research Chem 2009;2(2):196-201. [17] Reji TFAF, Devi SKC, Thomas KK, Sreejalekshmi KG, Manju SL, Rajasekharan KN. Synthesis and cytotoxicity studies of thiazoles analogs of the anticancer marine alkaloid dendrodine. Ind J Chem 2008;47B: 1145-1150. [18] Quing Z, Chao S, Hui Z, Jinchao Z, Pengfei Z. Synthesis, Carbohydrate Research 2010; 345: 437-441. [19] Venkateshwar TK, Rao KS, Dubey PK. Ind J Chem 2007;46B: 1033-1037. [20] Unanget P, Conner D, Cetenko W, Sorenson R, Kostlan C, Sircar J. J Med Chem 1994; 37: 322-328.

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Amrita A Zagade et al Der Pharma Chemica, 2011, 3 (1):523-537 ___________________________________________________________________________ [21] Reddy G, Rao K. Ind J Chem 2006;45B: 2143-2146. [22] Pande A, Saxena VK. Ind J Pharm Sci 1985: 689-692. [23] Pattanaik J, Pattanaik M, Bhatta D. Ind J Chem 1998;37B: 1304-1306. [24] Hui L, Zongcheng L, Thoreleif A. Molecules 2000; 5: 1055-1061. [25] Takeo F, Shigeyuki C, Naoya K, Yoshiko S, Ryoko Y, Toshihito K. In vitro and In vivo pharmacological profile of 5-{2-[4-(6-floro-1H-indole-3-yl)piperidine-1-yl]ethyl}-4-(4fluorophenyl)thiazole-2-carboxylic acid amide (NRA0562), a novel and putative atypical antipsychotic. Life Sciences 2002; 71: 1371-1348.

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