Mecaptooxadiazole a Lead Molecule in the Medicinal Chemistry: A Review

 

Nachiket S. Dighe1*, Ravindra B. Saudagar2, Ramesh S. Kalkotwar3 and D. A. Jain4

1Department of Pharmaceutical Chemistry, Pravara Rural College of Pharmacy, Loni, MS, India-413736.

2Department of Pharmaceutical Chemistry, R.G. Sapkal College of Pharmacy, Nashik, M.S. India.

3Department of Pharmaceutical Chemistry, S.N.D. College of Pharmacy, Yeola, Dist-Nashik, MS, India.

4Department of Pharmaceutical Sciences and Research, Bhagwant University, Ajmer, Rajasthan, India

*Corresponding Author E-mail: nachiket1111@rediffmail.com

 

ABSTRACT:

Mercaptooxadiazole is a five membered heterocyclic system consists of two nitrogen and one oxygen atoms along with acidic thiol group. As it increases the acidity of the titled compounds. It can be easily synthesized from hydazides using potassium hydroxide in presence of carbon disulphide. Mercaptooxadiazoles posses wide spectrum of biological activities like antibacterial, antifungal, antiviral, anti-inflammatory, anticonvulsant, antidepressant, antihypertensive, analgesic, and hypoglycemic properties. The present review is an attempt made to reveal the therapeutic and synthetic profiles of the mercaptooxadiazole ring.

 

KEYWORDS: Mercaptooxadiazole, Synthesis, Biological evaluation.

 


INTRODUCTION:

Synthesis of Substituted Mercapto- 1,2,4- triazoles and Substituted 1,2,4- triazol- 5-ylmercaptomethyl – 1, 3, 4 – oxadiazoles as antimicrobial Agents.

Some amides, hydrazides and arylidene- hydrazides of ethyl 3, 4- disubstituted1,2,4- triazole- 5- mercaptoacetates have been prepare by reacting with alkylamines, hydrazine hydrate and reaction with aldehydes. The synthesized compounds were been teted against a number of pathogenic microorganisms and showed promising results.1

 

Synthesis and evaluation of new of 3-(5-mercapto- [1,3,4] oxadiazol-2yl methyl)- 3H-benzooxazol-2-one for their antibacterial activity

A mixture of (2-oxobenzooxazol-3yl) acetic acid hydrazide  KOH  and carbon disulphide in ethanol was refluxed on oil bath for 12 h to give 3-(5-mercapto- [1,3,4] oxadiazol-2yl methyl)- 3H-benzooxazol-2-one for their antibacterial activity.2

 

Synthesis and antimicrobial activities of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles and [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazines

Acetic acid hydrazides containing 1, 2, 4-triazol-3-one ring were synthesized by the reaction of compounds with hydrazine hydrate. (5-Mercapto-1,3,4-oxadiazol-2-yl)methyl- 2,4-dihydro-3H-1,2,4-triazol-3-one derivatives were obtained from the reaction of compounds  with carbon disulfide in the presence of KOH. The synthesized compounds show good antimicrobial activities.3

 

Synthesis and Evaluation Of Anti Ulcerogenic Studies of Some Novel and 3-Mercapto-1, 2, 4-Triazole

Synthesis of novel 3-mercapto-1, 2, 4-triazole derivatives of diclofenac acid along with their derivatives has been done.  The synthetic compounds showed good ulcerogenic activity.4

 

Synthesis and Antimicrobial Activity of 1-(5-Mercapto-1, 3, 4-Oxadiazol-2-yl) -2-(Pyridine-2-ylamino) ethanone

1-(5-Mercapto-1,3,4-oxadiazol-2-yl)-2-(pyridine-2-ylamino)ethanone, has been synthesized from 2-(pyridine-2-ylamino) acetohydrazide. A yellow colored compound was reacted with carbon disulfide and potassium hydroxide in absolute ethanol to obtain the 1-(5-mercapto-1, 3, 4-oxadiazol-2-yl)-2-(pyridine-2-ylamino) ethanone.The synthesized compounds were evaluated for their antimicrobial activity and were expressed as the corresponding minimum inhibitory concentration (MIC).5

 

 

Synthesis and biological screening of some new Substituted 2-mercapto-4-(3h)-quinazolinone

Analogs as anticonvulsant agents

A new series of 2-mercapto-3-(4-chlorophenyl)-4-oxo-6-iodoquinazoline was synthesized. The anticonvulsant activities of prepared compounds have been examined using the PTZ-seizure threshold test. Compounds showed a significant anticonvulsant activity.6

 

Rapid and efficient microwave-assisted synthesis of 4-amino-3-mercapto- 5-substituted-1,2,4-triazoles

Synthesis of 4-amino-3-mercapto-5-substituted-1,2,4-triazoles, building blocks for the synthesis of fused heterocycles, under microwave irradiation is demonstrated.7

 

Synthesis of Some New Substituted 2-Mercaptoquinazoline Analogs as Potential Antimicrobial Agents

A new series of substituted 2-mercapto-3-(4-chlorophenyl)-6-iodo-3H-quinazolin-4- ones was prepared and screened for antimicrobial activity. A detailed synthesis of new 2- mercaptoquinazolinones and their antimicrobial screening are reported 8

 

 

Antioxidant Activity of Some Substituted 1, 2, 4 - Triazo-5-thione Schiff base

Series of Schiff’s bases of 3-substituted 1, 2, 4 triazo -5 thione were synthesized from the ester of methyl paraben. All the compounds were evaluated for its antioxidant activity by hydrogen peroxide scavenging method. The result shows that all the compounds have good bio availability and have significant antioxidant activity.9

 

Microwave assisted synthesis of Potential anti infective and anticonvulsant Thiosemicarbazones

1, 2, 4-triazole nucleus is therapeutically interesting drug candidate as anti-inflammatory, anti-infective and

CNS stimulant. Heteroaryl semicarbazones and thiosemicarbazone have emerged as structurally novel anticonvulsants and found to possess antifungal properties and anti-HIV properties. Therefore thiosemicarbazide derivatives of 5-mercapto-3-(3’- pyridyl)-4H-1, 2, 4-triazole 4 were synthesized.10

 

Synthesis and Antimicrobial Activity of New 5-(2-Thienyl)-1, 2, 4- triazoles

New 5-(2-thienyl)-1,2,4-triazoles and 5-(2-thienyl)-1,3,4-oxadiazoles namely, N-[3-mercapto-5-(2-thienyl)-1,2,4-triazol-4-yl]-N'-arylthioureas were prepared. The synthesized compounds were tested for in vitro activities against certain strains of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans.11

 

Bis(mercaptoazoles)

The reactions with mercaptoazoles namely, zis(mercaptotriazoles), bis(mercaptooxadiazoles), and bis(mercaptothiadiazoles) in 2 : 1 molar ratio, respectively, have been studied in dry tetrahydrofuran in the presence of n-butylamine and the binuclear complexes of the type  are obtained. Tentative structural conclusions are drawn for the reaction products based upon elemental analysis, electrical conductance, magnetic moment, and spectral data (UV-Vis, IR, 1H NMR, and 13C NMR). FAB-mass spectra of few complexes of each series were also carried out to confirm the binuclear structures. Studies were conducted to assess the growth-inhibiting potential of the complexes synthesized, and the ligands against various fungal and bacterial strains.12

 

Synthesis of New 1, 2, 4 Triazoles the Mercapto and Thione Substituted 1,2,4 Triazole Derivatives:

New 1,2,4triazoles  the mercapto and thionesubstituted 1,2,4 triazole ring systems have been well studied and a variety of biological activities have been reported for a large number of their derivatives, such as antiproliferative, antimicrobial, antifungal,  anticancer properties. In addition, mercapto1, 2, 4triazoles are also of great utility to prepare other heterocyclic compounds.13

 

Synthesis, Antibacterial, Antifungal and Genotoxic activity of Bis-1, 3 4-Oxadiazole Derivatives

The compounds are: 5,5’-dimercapto- bis-[1,3,4-oxadiazol-2-yl]propane, 5,5’-dimercapto-bis-[1,3,4- oxadiazol-2-yl]butane, 5,5’-dimercapto-bis-[1,3,4-oxadiazol-2-yl]octane were synthesized. The synthesized compounds showed good antibacterial activity.14

 

 

CONCLUSION:

The concept of the research lied in this review is to direct the attention of the researchers towards the development of newer drug candidate for the treatment of various life threatening diseases and disorders. Medicinal chemist s should consider mercaptooxadiazole as a candidate for the development of newer lead molecules as it  posses wide spectrum of biological activities and are easy to synthesize as compared to the other heterocycles.

 

REFERENCES:

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7.        SS Joshi and A V Karnik, Rapid and efficient microwave-assisted synthesis of 4-amino-3-mercapto- 5-substituted-1,2,4-triazoles, Indian Journal of Chemistry, Vol. 45B, April 2006, pp. 1057-1059

8.        Adel S. El-Azab, Synthesis of Some New Substituted 2-Mercaptoquinazoline Analogs as Potential Antimicrobial Agents, Phosphorus, Sulfur, and Silicon, 182:333–348, 2007

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10.     Aniket Kshirsagar, Mrunmayee P Toraskar, Microwave assisted synthesis of Potential anti infective and anticonvulsant Thiosemicarbazones, Int.J. ChemTech Res.2009,1(3) 696-701.

11.     Mohamed A. Al-Omar, Synthesis and Antimicrobial Activity of New 5-(2-Thienyl)-1,2,4- triazoles and 5-(2-Thienyl)-1,3,4-oxadiazoles and Related Derivatives, Molecules 2010, 15, 502-514.

12.     Shilpi Sinha, Akhilesh Kumar Srivastava, Synthesis, Spectroscopic, and Antimicrobial Studies of Binuclear Metallocene (M = Ti, Zr, or Hf) Derivatives of Bis(mercaptoazoles), Bioinorganic Chemistry and Applications Volume 2007, Article ID 87918, 9 pages

13.     Sattar Ebrahimi , Synthesis of New 1, 2, 4 Triazoles the Mercapto and Thione Substituted 1,2,4 Triazole Derivatives, European Journal of Chemistry 1 (4) (2010) 322324.

14.     Ahmed O. Maslat, Mahmud Abussaud,, Synthesis, Antibacterial, Antifungal and Genotoxic activity of Bis-1, 3 4-Oxadiazole Derivatives, Pol. J. Pharmacol., 2002, 54, 55–59.

 

 

 

Received on 11.12.2011          Accepted on 20.12.2011        

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Asian J. Res. Pharm. Sci. 1(4): Oct.-Dec. 2011; Page 93-96