Biologically Active 2,5-Disubstituted-1,3,4-Oxadiazoles
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https://doi.org/10.37285/ijpsn.2009.2.1.2Abstract
There are vast numbers of pharmacologically active heterocyclic compounds in regular clinical use. The presence of heterocyclic structures in diverse types of compounds is strongly indicative of the profound effects such structure exerts on physiologic activity, and recognition of this is abundantly reflected in efforts to find useful synthetic drugs. The 1,3,4-oxadiazole nucleus has emerged as one of the potential pharmacophore responsible for diverse pharmacological properties. Medical Literature is flooded with reports of a variety of biological activities of 2,5-Disubstituted-1,3,4-oxadiazoles. The present work is an attempt to summarize and enlist the various reports published on biologically active 2,5-disubstituted-1,3,4-oxadiazoles.
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1,3,4-oxadiazoles, anti-inflammatory activity, hypoglycemic activity, anticonvulsant activity, antiallergic activity, antimicrobial activity, anticancer activity
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Abadi AH, Eissa AA and Hassan GS. Synthesis of novel 1,3,4-trisubstituted pyrazole derivatives and their evaluation as antitumor and antiangiogenic agents. Chem. Pharm. Bull. 51: 838–844 (2003).
Aboraia AS, Abdel-Rahman HM, Mahfouz NM and EL-Gendy MA. Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: Promising anticancer agents. Bioorg. Med. Chem. 14: 1236–1246 (2006).
Adelstein GW, Yen CH, Dajani EZ and Bianchi RG. 3,3-diphenyl-3-(2-alkyl-1,3,4-oxadiazol-5-yl)-propylcycloakylamines, a novel series of antidiarrheal agents. J. Med. Chem. 19(10): 1221–1225 (1976).
Adelstein GW. Antiarrythmic agents. Synthesis and biological activity of some tetrazole and oxadiazole analogs of 4-dialkylamino-2,2-diarylbutyramides. J. Med. Chem. 16: 309–312 (1973).
Almasirad A, Tabatabai SA, Faizi M, Kebriaeizadeh A, Mehrabai N, Dalvandi A and Shafiee A. Synthesis and anticonvulsant activity of new 2-substituted-5-[2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles. Bioorg. Med. Chem. Lett. 14: 6057–6059 (2004).
Amir M and Shikha K. Synthesis and anti-inflammatory, analgesis, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6-dichloroanilino)phenyl]acetic acid derivatives. Eur. J. Med. Chem. 39: 535–545 (2004).
Andotra CS, Langer TC and Sharma SK. Synthesis of some nitro-substituted 1,3,4-oxadizoles, 1,3,4-thiadiazoles and 1,2,4-triazoles as antiamebic agents. J. Indian Chem. Soc. 66: 122–123 (1989).
Andotra CS, Langer TC, Sharma SK and Sarin AN. Synthesis and antibacterial activities of some substituted oxadiazoles, thiadiazoles and triazoles. Indian J. Pharm. Sci. 48: 192–195 (1986).
Ates O, Kocabalkanli A, Otuk G, Ekinci AC and Vidin A. Synthesis and antibacterial activity of 5-aryl-2-[(α-chloro-α-phenylacetyl/α-bromopropionyl)amino]-1,3,4-oxadiazoles and 2-[(5-aryl-1,3,4-oxadiazol-2-yl)imino]-5-phenyl/methyl-4-thiazolidinones. Arzneim-Forsch. 47: 1134 (1997).
Ates O, Kocabalkanli N, Cesur N and Otuk G. Synthesis and antimicrobial activity of some 5-aryl-2-[(N, N-disubstituted thiocarbamoylthio)acylamino]-1,3,4-oxadiazoles. Il Farmaco 53:541–544 (1998).
Boschelli DH, Connor DT, Bornemeier DA, Dyer RD, Kennedy JA, Kuipers PJ, Okonkwo GC, Schrier DJ and Wright CD. 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole analogs of the fenamates: In-vitro inhibition of cyclooxygenase and 5-lipoxygenase activities. J. Med. Chem. 36: 1802–1810 (1993).
Burbuliene MM, Jakubkiene V, Mekuskiene G, Udrenaite E, Smicius R and Vainilavicius P. Synthesis and anti-inflammatory activity of derivatives of 5-[(2-disubstitutedamino-6-methyl-pyrimidin-4-yl)-sulfanyl methyl]-3H-1,3,4-oxadiazole-2-thiones. Il Farmaco 59: 767–774 (2004).
Cao S, Qian X, Song G and Huang Q. Synthesis and insecticidal activity of new 2-(5-(trifluoromethyl) pyridyloxymethyl)-1,3,4-oxadiazoles. J. Fluorine Chem. 117:63–66 (2002).
Chaoudhari BR, Shinde DB and Shingare MS. Synthesis of some 1,4-benzothiazinyl thiosemicarbazides, triazoles, oxadiazoles, thiadiazoles and their antitubercular activity. Indian J. Heterocyclic Chem. 4: 187–190 (1995).
Chen H, Li Z and Han Y. Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl-(alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (Thiadiazoles). Agric. Food Chem. 48: 5312–5315 (2000).
Choudhary SK, Choudhary M, Choudhary A and Parmar SS. Anticonvulsant and antiproteolytic properties of 3,5-disubstituted oxadiazole-2-thiones and their inhibition of respiration in rat brain homogenates. J. Pharm. Sci. 67(11): 1507–1509 (1978).
Dabhi TP, Shah VH and Parikh AR. Studies on 1,3,4-oxadiazoles: Preparation and antimicrobial activity of 2-mercapto-/carboxy-methylthio-5-(3'-arylamino-sulfophenyl)-1,3,4-oxadiazoles. Indian J. Pharm. Sci. 54: 98–100 (1992).
Dighe VS, Bagavant G, Somasekhara S and Mukherjee SL. Substituted oxadiazole-2-thiones. Curr. Sci. 32: 257 (1963).
Dutta MM, Goswami BN and Katky JCS. Studies on biologically active heterocycles. Part I. Synthesis and antifungal activity of some new aroyl hydrazones and 2,5-disubstituted-1,3,4-oxadiazoles. J. Heterocyclic Chem. 23: 793–795 (1986).
El-Emam AA, Al-Deeb OA, Al-Omar M and Lehmann J. Synthesis, antimicrobial and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substitutedthio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones. Bioorg. Med. Chem. 12: 5107–5113 (2004).
Gaonkar SL, Rai KML and Prabhuswamy B. Synthesis and antimicrobial studies of a new series of 2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-5-substituted-1,3,4-oxadiazoles. Eur J. Med. Chem. 41: 841–846 (2006).
Girges MM. Synthesis and pharmacological evaluation of novel series of sulfonate ester-containing 1,3,4-oxadizole derivatives with anticipated hypoglycemic activity. Arzeim-Forsch. 44: 490 (1994).
Goswami BN, Kataky JCS, Baruah JN and Nath SC. Synthesis of 3,5-disubstituted-1,3,4-oxadiazole-2-thiones as potential fungicidal agents. J. Heterocycl. Chem. 21: 205–208 (1984).
Hanna MA, Girges MM, Rasala D and Gawinecki R. Synthesis and pharmacological evaluation of some novel 5-(pyrazole-3-yl)thiadiazole and oxadiazole derivatives as potential hypoglycemic agents. Arzneim-Forsh. 45: 1074–1078 (1995).
Harfenist M, Heuser DJ, Joyner CT, Batchelor JF and White HL. Selective inhibitors of monoamine oxidase. 3.structure activity relationship of tricyclics bearing imidazoline, oxadiazole or tetrazole groups. J. Med. Chem. 39: 1857–1863 (1996).
Hiu X-P, Zhang L-M, Zhang Z-Y, Wang Q and Wang F. Synthesis and antibacterial activities of 1,3,4-thiadiazole, 1,3,4-oxadiazole and 1,2,4-triazole derivatives of 5-methylisoxazole. Indian J. Chem. 38B: 1066–1069 (1999).
Hokfelt B and Joensson A. Hypoglycemic activity in relation to chemical structure of potential oral antidiabetic substances. III. 2-benzenesulfonamido-5-alkyl-1,3,4-thiadiazoles and oxadiazoles. J. Med. Chem. 5: 247–256 (1962).
Holla BS, Prasanna CS, Poojary B, Rao KS, Shridhara K and Bhat UG. Synthesis and insecticidal activity of number of 1,3,4-oxadiazoles derived from 2-chloropyridine-5-acetic acid. Indian J. Chem. 43B:864–868 (2004).
Husain MI and Shukla MK. Search for potent anthelmintics. Part VIII: 4-substituted-7-coumarinyloxyacetyl thiosemicarbazides and 7-coumarinyloxy methyl-1,2,4-triazoles and 1,3,4-oxadiazoles. J. Indian Chem. Soc. 55: 826–828 (1978).
Husain MI, Kumar A and Srivastava RC. Synthesis of N-(2-naphthyloxyacetyl)-thiosemicarbazides and 2-arylamino-5-(2-naphthyloxymethyl)-1,3,4-thiadiazoles/ oxadiazoles as oral hypoglycemic agents. Curr. Sci. 55(14): 644–646 (1986).
Husain, M.K. and Jamali, M.R., Synthesis and pharmacological evaluation of N1-(p-(3-aryl-4-oxaquinazolin-2-yl-methyl-amino)benzoyl)-N4-arylthio-semicarbazides and 2-arylamino-5-(p-(3-aryl-4-oxaquinazolin-2-yl-methylamino)phenyl)-1,3,4-thiadiazole/oxadiazoles as oral hypoglycemic agent. Indian J. Chem. 27B: 43 (1988).
Jakubkiene V, Burbuliene MM, Mekuskiene G, Udrenaite E, Gaidelis P and Vainilavicius P. Synthesis and anti-inflammatory activity of 5-(6-methyl-2-substituted-4-pyrimidyloxymethyl)-1,3,4-oxadiazole-2-thiones and their 3-morpholinomethyl derivatives. Il Farmaco 58: 323–328 (2003).
Kachroo PL, Gupta K, Gupta SC and Gupta AK. Synthesis of some substituted-1,3,4-oxadiazoles, their antibacterial, antiamebic activity. Nat. Acad. Sci. Lett. 13: 125–126 (1990).
Kadi AA, El-Brollosy NR, Al-Deep OA, Habib EE, Ibrahim TM and El-Emam AA. Synthesis, antimicrobial and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. Eur. J. Med. Chem. 42(2): 235–242 (2007).
Kalluraya B and Chimbalkar R. Synthesis and biological activity of some 5-substituted-1,3,4-oxadiazole-2-hydrazones. Indian J. Heterocylc Chem. 5: 37–40 (1995).
Kalsi R, Pande K and Barthwal JP. Synthesis of formazans of substituted oxadiazole-2-(3H)-thiones. Indian J. Chem. 27B: 197–199 (1988).
Kapoor KK, Somal P, Gupta R and Kachroo PL. Synthesis and antimicrobial activity of some 5-aryl-2-[N-(5-nitrofurfurylidene)amino]- and 5-aryl-2-(N-(5-thiocarbomylamino)-1,3,4-oxadiazoles. J. Indian Chem. Soc. 68: 104–106 (1991).
Khan MTH, Choudhary MI, Khan KM, Rani M and Rahman AU. Structure-activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues. Bioorg. Med. Chem. 13: 3385–3395 (2005).
Khanum SA, Shashikanth S, Umesha S and Kavitha R. Synthesis and antimicrobial study of novel heterocyclic compounds from hydroxybenzophenones. Eur. J. Med. Chem. 40(11): 1156–1162 (2005).
Kim RM, Rouse EA, Chapman KT, Schleif WA, Olsen DB, Stahlhut M, Rutkowski CA, Emini EA and Tata JR. P1' oxadiazole protease inhibitors with excellent activity against native and protease inhibitor-resistant HIV-1. Bioorg. Med. Chem. 14: 4651–4654 (2004).
Kishore V, Kumar S, Parmar SS and Senburg VI. Anti-inflammatory and antiproteolytic properties of naphthylthiosemicarbazides and cyclized oxadiazoles. Res. Commun. Chem. Pathol. Pharmacol. 11: 581–594 (1975).
Kramer JB, Boschelli DH, Connor DT, Kostlan CR, Kuipers PJ, Kennedy JA, Wright CD, Bornemeier DA and Dyer RD. Cyclooxygenase and 5-lipoxygenase inhibitory activity of 2,6-di-t-butylphenols linked by a sulfur atom to 1,3,4-oxadiazoles. Bioorg. Med. Chem. Lett. 3: 2827–2830 (1993).
Kramer VI and Schunack W. Synthesis and H2-antagonistic activity of N,N-substituted 1,3,4-oxadiazole-2,5-diamines. Arzneim-Forsch. 36(2): 1564–1567 (1986).
Kucukguzel SG, Oruc EE, Rollas S, Sahin F and Ozbek A. Synthesis, characterization and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur. J. Med. Chem. 37: 197–206 (2002).
Kumar A, Singh S, Verma M, Saxena AK and Shankar K. Potent anti-inflammatory 2-(o-hydroxyphenyl)-5-(p-dimethylaminophenyl)-1,3,4-oxadiazoles. Indian. J. Pharm. Sci. 49(6): 201–204 (1987).
Li Y, Liu J, Zhang H, Yang X and Liu Z. Stereoselective synthesis and fungicidal activities of (E)-α-(methoxyimino)-benzene acetate derivatives containing 1,3,4-oxadiazole ring. Bioorg. Med. Chem. Lett. 16: 2278–2282 (2006).
Liu Z, Yang G and Qin X. Synthesis and biological activities of novel diheterocyclic compounds containing 1,2,4-triazolo[1,5-a]pyrimidine and 1,3,4-oxadiazole. J. Chem. Technol. Biotechnol. 76: 1154–1158 (2001).
Loetchutinat C, Chau F and Mankhetkorn S. Synthesis and evaluation of 5-aryl-3-(4-hydroxphenyl)-1,3,4-oxadiazole-2-(3H)-thiones as P-glycoprotein inhibitors. Chem. Pharm. Bull. 51: 728–730 (2003).
Macaev F, Rusu G, Pogrebnoi S, Gudima A, Stingaci E, Vlad L, Shvets N, Kandemirli F, Dimoglo A and Reynolds R. Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure anti-mycobacterial activities. Bioorg. Med. Chem. 13: 4842–50 (2005).
Mamolo MG, Zampieri D, Vio L, Fermeglia M, Ferrone M, Pricl S, Scialino G and Banfi E. Antimycobacterial activity of new 3-substituted 5-(pyridine-4-yl)-3H-1,3,4-oxadiazol-2-one and 2-thione derivatives. Preliminary molecular modeling investigations. Bioorg. Med. Chem. 13: 3797–3809 (2005).
Maslat AO, Abussaud M, Tashtoush H and Mahmoud AT. Synthesis, antibacterial, antifungal and genotoxic activity of Bis-1,3,4-oxadiazole derivatives. Pol. J. Pharmacol. 54: 55–59 (2002).
Mazouz F, Guiddari S, Burstein C, Mansuy D and Milcent R. 5-[4-(Benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives and related analogues: New reversible, highly potent and selective monoamine oxidase type B inhibitors. J. Med. Chem. 36: 1157–1167 (1993).
Mazouz F, Lebreton L, Milcent R and Burskin C. 5-Aryl-1,3,4-oxadiazol-2-(3H)-one derivatives and sulfur analogues as new selective and competitive monoamine oxidase type B inhibitors. Eur. Med. Chem. 25: 659–671 (1990).
Mehta L and Parekh H. Studies on ureas. Part-I Preparation and antimicrobial activity of N'-aryl-N3-2-p-chlorophenyl-1,3,4-oxadiazol-5-ylacylureas. Indian J. Chem. Soc. 65: 521–522 (1988).
Miara HK. Synthesis of some new substituted 1,3,4-oxadiazoles as potential insecticidal, antibacterial and anti-acetylcholine esterase agents. Arch. Pharm. 316: 487–493 (1983).
Mir I, Siddiqui MT and Comrie AM. Antituberculosis agents. Part II. α-[5-(2-furyl)-1,3,4-oxadiazol-2-yl-thio]acetohydrazide and related compounds. J. Chem. Soc. 16: 2798–2799 (1971).
Misra U, Hitkari A, Saxena AK, Gurtu S and Shanker K. Biologically active indolylmethyl-1,3,4-oxadiazoles, 1,3,4-thiadiazoles, 4H-1,3,4-triazoles and 1,2,4-triazines. Eur. J. Med. Chem. 31: 629–634 (1996).
Morvin M and Maysinger D. Synthesis and biological activity of some N-dialkyl-amino methyl oxadiazolines and oxadiazolthiones. Die Pharmazie 38: 561 (1983).
Mullican MD, Wilson MW, Connor DT, Kostlan CR, Schrier DJ and Dyer RD. Design of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)- 1,3,4-thiadiazoles, -1,3,4-oxadiazoles and -1,2,4-triazoles as orally-active, nonnulcerogenic anti-inflammatory agents. J. Med. Chem. 36: 1090–1099 (1993).
Najer H, Giudicelli R, Morel C and Menin J. Synthesis of some 5-aryl-2-dimethylamino-1,3,4-oxadiazoles endowed with anti-inflammatory properties. Bull. Soc. Chim. Fr. 1: 153–159 (1966).
Nargund LVG, Reddy GRN and Hariprasad V. Anti-inflammatory activity of substituted 1,3,4-oxadiazoles. J. Pharm. Sci. 83: 246–248 (1994).
Nath SC. Synthesis of 3,5-disubstituted 1,3,4-oxadiazol-2-thiones as potential fungicidal agents. J. Heterocyclic Chem. 21: 205–208 (1984).
Nigam R, Swarup S, Saxena VK and Singh HK. Synthesis and pharmacological screening of some new 2- thio-3-(substituted-aminomethyl)-5-(3,5-dinitrophenyl)-1,3,4-oxadiazoles. J. Indian Chem. Soc. 69: 692–693 (1992).
O’neal JB, Rosen H, Russell PB, Adams AC and Blumenthal A. Potential hypoglycemic agents: 1,3,4-oxadiazoles and related compounds. J. Med. Pharm. Chem. 91: 617–26 (1962).
Omar AMME and Aboulwafa OM. Synthesis and anticonvulsant properties of a novel series of 2-substituted amino-5-aryl-1,3,4-oxadiazole derivatives. J. Heterocyclic Chem. 21: 1415–1418 (1984).
Omar FA, Manfouz NM and Rahman MA. Design, synthesis and anti-inflammatory activity of some 1,3,4-oxadiazole derivatives. Eur. J. Med. Chem. 31: 819–825 (1996).
Palaska E, Sahin G, Kelicen P, Durlu NT and Altinok G. Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazole-2-thiones. Il Farmaco 57: 101–107 (2002).
Palomer A, Cabre F, Pascual J, Campos J, Trugillo MA, Entrena A, Gallo MA, Garcia L, Macleon D and Espinosa A. Identification of novel cyclooxygenase-2 selective inhibitors using pharmacophore models. J. Med. Chem. 45: 1402–1411 (2002).
Pancechovska-ksepko D, Foks H, Landowska E, Janowiec M and Zwolska-kwiek Z. Pyridine derivatives XVII Synthesis and tuberculostatic activity of pyrazinyl-1,3,4-oxadiazole derivatives. Acta. Pol. Pharm. 43: 116–123 (1986).
Pramanik SS and Mukherjee A. Synthesis and in-vitro serotonin-3-antagonist activities of some new 1,3,4-oxadiazole-2-thiones. J. Indian Chem. Soc. 75: 53–54 (1998).
Puglisi G, Pignatello R, Panico A, Mazzone G, Corsaro A, Caruso A, Leone MG and Amico-Roxas M. Synthesis and biological evaluation of 2-alkoxyphenyl-6-(substitutedphenyl)-1,3,4-thiadiazole-[3,2-a]-s-triazin-5,7-diones and 1-(alkyl and substitutedphenyl)-3-[5-alkoxyphenyl-1,3,4-thia- and oxadiazole-2-yl]-ureas. Eur. J. Med. Chem. 24: 277–286 (1989).
Radha Rani B, Bhalerao VI and Rahman MF. Synthesis and biological activity of benzothiazolothiomethyloxadiazoles, -thiadiazoles and -triazoles. Indian J. Chem. 29B: 995–998 (1990).
Rai KML and Linganna N. Synthesis and evaluation of antimitotic activity of alkylated 2-amino-1,3,4-oxadiazole derivatives. Il Farmaco 55: 389–392 (2000).
Rajak H, Kharya MD and Mishra P. Synthesis and Local Anesthetic Activity of Some Novel N-[5-(4-Substituted) phenyl-1,3,4-oxadiazol-2-yl]-2-(Substituted)-Acetamides. Arch. Pharm. 341(4): 247–261 (2008).
Rajak H, Kharya MD and Mishra P. Synthesis of some novel oxadiazole and oxadiazoline analogues for their Anti-inflammatory activity. Yaku Zasshi. 127(10): 1757–1764 (2007).
Ramalingam T and Sattur PB. Synthesis and anti-inflammatory activity of benzal-3-penta decylaryloxyalkyl carboxylic acid hydrazides and 2-benzalamino-5-(3'-pentadecylaryloxylalkyl)-1,3,4-oxadiazoles. Eur. J. Med. Chem. 25: 541–544 (1990).
Ramalingam T, Deshmukh AA and Sattur PB. Synthesis and pharmacology of 2,5-disubstituted-1,3,4-oxadiazoles. J. Indian Chem. Soc. 58: 269-271 (1981).
Raman K, Parmar SS and Sulzman SK. Anti-inflammatory activity of substituted 1,3,4-oxadiazoles. J. Pharm. Sci. 78(12): 999–1002 (1989).
Raman K, Singh HK, Salzman SK and Parmar SS. Substituted thiosemicarbazides and corresponding cyclized 1,3,4-oxadiazoles and their anti-inflammatory activity. J. Pharm. Sci. 82: 167–169 (1983).
Ramlingam T and Sattur PB. Synthesis and biological evaluation of α-(3-pentadecylaryloxy)-propionic acids, their hydrazides and cyclic derivatives: oxadiazoles and pyrroles. Indian Drugs 24(11): 514–517 (1987).
Sahin G, Palaska E, Ekizoglu M and Ozalp M. Synthesis and antimicrobial activity of some 1,3,4-oxadiazole derivatives Il Farmaco 57: 539–542 (2002).
Sawhney SN and Gupta A. Synthesis of some 2-(5-substituted-1,3,4-oxadiazol-2-yl)-, 2-(5-substituted-1,3,4-thiadiazol-2-yl)- and 2-(3-mercapto-4-substituted-4H-1,2,4-triazol-5-yl)-benzimidazoles as potential anti-inflammatory agents. Indian J. Chem. 30B: 407–412 (1991).
Saxena S, Verma M, Saxena AK and Shanker K. 1,3,4-oxadiazolethiones as inflammation inhibitors. Indian J. Pharm. Sci. 54: 1–3 (1992).
Schrier DJ, Baragi VM, Connor DT, Dyer RD, Jordan JH, Imre KM, Lesch ME, Mullican MD, Okonkwo GCN and Conroy MC. The Phramacologic effects of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2(3H)-thione choline salt (CI-986), a novel inhibitor of arachidonic acid metabolism in models of inflammation. Prostaglandins 47: 17–30 (1994).
Sengupta A K and Singh B. Studies on potential pesticides. Part X. Synthesis of some 2,5-disubstituted-1,3,4-oxadiazoles. Indian J. Pharm. Sci. 41: 48–50 (1979).
Sengupta AK, Garg M and Chandra U. Synthesis of some new mannich bases derived from substituted benzimidazole, benzoxazol-2-one, benzoxazol-2-thione, oxadiazole-2-thiones and their biological activities. J. Indian Chem. Soc. 56: 1230–1232 (1979).
Sharma RS and Bahel SC. Synthesis of aryloxy/aryl acetyl thiosemicarbazides, substituted 1,3,4-oxadiazoles, 1,3,4-thiadiazoles, 1,2,4-triazoles and related compounds as potential fungicides. J. Indian Chem. Soc. 59: 877–880 (1982).
Sherman WR. 5-nitro-2-furyl-substituted-1,3,4-oxadiazole, 1,3,4-thiadiazoles and 1,3,5-triazines. J. Org. Chem. 26:88–95 (1961).
Shi W, Qian X, Song G, Zhang R and Li R. Synthesis and insecticidal activities of novel 2-fluorophenyl-5-aryl/cyclopropyl-1,3,4-oxadiazoles. J. Fluorine Chem. 106: 173–179 (2000).
Shi W, Qian X, Zhang R and Song G. Synthesis and quantitative structure-activity relationships of new 2,5-disubstituted-1,3,4-oxadiazoles. J. Agric. Food Chem. 49: 124–130 (2001).
Shukla MK, Singh SP and Agrawal VK. Synthesis and biological activity of some hydrazones and uredo oxadiazoles of 4-acetamido phenoxyacetic acid hydrazide. Curr. Sci. 49: 936–938 (1980).
Singh HH, Nagar S, Chaudhari A and Parmar SS. Inhibition of pyruvic acid oxidation by 2, 5-disubstituted-1,3,4-oxadiazoles. J. Pharm. Sci. 62: 504–507 (1973).
Singh IP, Saxena AK and Shankar K. Synthesis and anti-inflammatory activity of oxadiazolines thione hydrochlorides. Eur. J. Med. Chem. Chim. Ther. 21(3):267–269 (1986).
Smith CJ, Zhang Y, Koboldt CM, Muhammad J, Zweifel BS, Shaffer A, Talley JJ, Masferrer JL, Seibert K and Isakson PC. Pharmacological analysis of cyclooxygenase-1 in inflammation. Proc. Natl. Acad. Sci. USA 95: 13313–13318 (1998).
Soni N, Barthwal JP, Saxena AK, Bhargava KP and Parmar SS. Monoamine oxidase and succinate dehydrogenase inhibitory properties of substituted 1,3,4-oxadiazole-2-thiones. J. Heterocyclic Chem. 19: 29–32 (1982).
Suman SP and Bahel SC. Synthesis of 2-arylamino-5-aryl/aryloxymethyl-1,3, 4-thiadiazoles, N1-aryl/aryloxyacetyl-3-methyl-5-pyrazolones as possible fungicides. J. Indian Chem. Soc. 56: 374–376 (1979).
Szczepankiewicz BG, Liu G, Jae HS, Tasker AS, Gunawardana IW, Von Geldern TW, Gwartney SL II, Wu-wong JR, Gehrke L, Chiou WJ, Credo RB, Alder JD, Nukkala MA, Zielinski NA, Jarvis K, Mollison KW, Frost DJ, Bauch JL, Hiu Y H, Claiborne AK, Li Q and Rosenburg SH. New antimitotic agents with activity in multi-drug-resistant cell lines and in-vivo efficacy in murine tumor models. J. Med. Chem. 44: 4416–4430 (2001).
Talawar MB, Laddi UV. Synthesis and antimicrobial activity of some new 1,3,4-oxadiazoles and 1,2,4-triazoles. Indian J. Heterocycl. Chem. 4: 111–116 (1994).
Tan TMC, Chem Y, Kong KH, Bai J, Li Y, Lim SG, Ang TH and Lam Y. Synthesis and the biological evaluation of 2-benzene sulfonylalkyl-5-substituted-sulfanyl-[1,3,4]-oxadiazoles as potential anti-hepatitis B virus agents. Antiviral Research 71: 7–14 (2006).
Tan TMC, Chen Y, Kong KH, Bai J, Li Y, Lim SG, Ang TH and Lam Y. Synthesis and the biological evaluation of 2-benzenesulfonylalkyl-5-substituted-sulfanyl-[1,3,4]-oxadiazoles as potential anti-hepatitis B virus agents. Antiviral Research 71: 7–14 (2006).
Tewari RK, Mishra RK, Shrivastava S and Bahel SC. Synthesis of some new mannich bases, sulphides and disulphides of 1,3,4-oxadiazol-2-thiones as potential antifungal agents. J. Indian Chem. Soc. 68: 108–110 (1991).
Tozkoparan B, Gokhan N, Aktay G, Yesilada E and Ertan M. 6-benzylidenethiazolo[3,2-b]-1,2,4-triazole-5(6H)-ones substituted with ibuprofen: Synthesis, characterization and evaluation of anti-inflammatory activity. Eur. J. Med. Chem. 35: 743–750 (2000).
Tsitsa P, Papadaki-Valiraki A, Siatra-Papastaikoudi T, Papadopoulou-Doifoiti Z and Vamvakidis A. Synthesis and anticonvulsive activity of some new bisubstituted 1,3,4-oxadiazoles and 1H-1,2,4-triazoles. Ann. Pharm. Fr. 47: 296–303 (1989).
Warner TD, Giuliano F, Vaynovie I, Bukasa A, Mitchell JA and Vave JR. Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in- vitro analysis. Proc. Natl. Acad. Sci. USA 96: 7563–7568 (1999).
Wilder Smith AE. Preparation of some new 4-substituted derivatives of p-amino-o-hydroxyphenyl-1,3,4-oxadiazolone-5 and study of their mycobacteriostatic activity. VII. Arzneim-Forsch. 17(6): 768–772 (1967).
Wildersmith AE and Brodhage H. Biological spectrum of some new tuberculostatic 1, 3, 4-oxadiazolones with special reference to cross-resistance and rates of emergence of resistance. Nature 192: 1195 (1961).
Wildersmith AE and Frommel E. The preparation of some 1,3,4-oxadiazol-2-ols and oxadiazol-2-thiols active as tuberculostatics. Arzneim-Forsch. 12: 485–487 (1962).
Wildersmith AE, Brodhage H and Haukenes G. Some tuberculostatic 1,3,4-oxadiazolones(-5) and 1,3,4-oxadiazolthiones(-5). II: Biological spectrum in-vitro and activity in-vivo in relation to resistance emergence. Arzneim-Forsch. 12: 275–280 (1962).
Wildersmith AE, Frommel E and Radouco-thomas S. Preliminary screening of some new oxadiazol-2-ols with special reference to their antipyretic, analgesic, and anti-inflammatory properties V. Arzneim-Forsch. 13: 338–341 (1963).
Wildersmith AE. Metabolic pathway and its relationship to the biological activity of some tuberculostatic and leprostatic agents. Leprosy Rev. 35(3): 55–60 (1964).
Wildersmith AE. Preparation of some new 4-substituted derivatives of p-amino-o-hydroxyphenyl-1,3,4-oxadiazolthiones-5 and study of their mycobacteriostatic activity. Arzneim-Forsch. 17(9): 1150–1151 (1967).
Zarghi A, Faizi M, Shafaghi B, Ahadian A, Khojastehpoor HR, Zangaheh V, Tabatabai SA and Shafiee A. Design and synthesis of new 2-substituted-5-(2-benzylthiophenyl)-1,3,4-oxadiazoles as benzodiazepine receptor agonists. Bioorg. Med. Chem. Lett. 15: 3126–3129 (2005).
Zarghi A, Hajimahdi Z, Mohebbi S, Rashidi H, Mozaffari S, Sarraf S, Faizi M, Tabatabaee SA, Shafiee A. Design and synthesis of new 2-substituted-5-[2-(2-halobenzyloxy)phenyl]-1,3,4-oxadiazoles as anticonvulsant agents. Chem. Pharm. Bull. 56(4): 509–12 (2008).
Zarghi A, Tabatabai SA, Faizi M, Ahadian A, Navabi P, Zanganeh V and Shafiee A. Synthesis and anticonvulsant activity of new 2-substituted-5-(2-benzyloxyphenyl)-1,3,4-oxadizoles. Bioorg. Chem. Lett. 15: 1863–1865 (2005).
Zheng X, Li Z, Wang Y, Chen W, Huang Q, Liu C and Song G. Synthesis and insecticidal activities of novel 2,5-disubstituted-1,3,4-oxadiazoles. J. Fluorine Chem. 123: 163–169 (2003).
Zou XJ, Lai L-H, Jin G-Y and Zhang Z-X. Synthesis, fungicidal activity and 3D-QSAR of pyridazinone-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles. Agric. Food Chem. 50: 3757–3760 (2002).
Zou XJ, Lai LH, Jin GY and Zhang ZX. Synthesis, fungicidal activity, and 3D-QSAR of pyridazinone-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles. J. Agric. Food Chem. 50: 3757–3760 (2002).
