ChemInform Abstract: Synthesis of 2,5‐Disubstituted 1,3,4‐Oxadiazoles as Biologically Active Heterocycles.

Kagthara, Preeti; Shah, Niraj S.; Doshi, Rajeev; Parekh, H.

doi:10.1002/chin.199943127

Cited by 20 publications

(20 citation statements)

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“…The 1,3,4-oxadiazoles have been found to exhibit diverse biological activities such as antimicrobial [29][30][31][32][33], antitubercular [34], antioxidant [35], antimalarial [36], analgesic [37], anti-inflammatory [38,39], anticonvulsant [40], hypoglycemic [41] activities, as well as other biological properties such as genotoxic [42] and lipid peroxidation inhibitory activities [43]. Two examples of compounds containing the 1,3,4-oxadiazole ring used in clinical medicine are raltegravir, an antiretroviral drug [44] and zibotentan, an anticancer agent [45] (Figure 2).…”

Section: (Figure 2) Also N-(5-(cyano(4-methyl-3-phenylthiazol-2(3h)-mentioning

confidence: 99%

Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

Shaker

Marzouk

2016

Molecules

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A (pyridazinyl)acetate derivative was reacted with thiosemicarbazide and hydrazine hydrate to yield spiropyridazinone and acetohydrazide derivatives, respectively. The acetohydrazide derivative was used as a starting material for synthesizing some new heterocyclic compounds such as oxoindolinylidene, dimethylpyrazolyl, methylpyrazolyl, oxopyrazolyl, cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives. The behavior of the cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives towards nitrogen and carbon nucleophiles was investigated. The assigned structures of the prepared compounds were elucidated by spectral methods (IR, 1 H-NMR 13 C-NMR and mass spectroscopy). Some of the newly prepared compounds were tested in vitro against a panel of four human tumor cell lines, namely hepatocellular carcinoma (liver) HePG-2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. Also they were tested as antioxidants. Almost all of the tested compounds showed satisfactory activity.

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Section: (Figure 2) Also N-(5-(cyano(4-methyl-3-phenylthiazol-2(3h)-mentioning

confidence: 99%

Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

Shaker

Marzouk

2016

Molecules

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“…Kagthara et al have synthesized some 2-azetidinone derivatives which showed a potential antitubercular activity [46]. The synthesized compounds were tested in vitro for their antitubercular activity against Mycobacterium tuberculosis H 37 RV.…”

Section: Antitubercular Activitymentioning

confidence: 99%

2-Azetidinone – A new profile of various pharmacological activities

Mehta

Sengar

Pathak

2010

European Journal of Medicinal Chemistry

187

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“…It also exhibits many biological activities like antihypertensive [7,8], anti-inflammatory [9], endocannabinoid metabolism inhibitor, antibiotic [10] and anticonvulsant [11]. 1,3,4-Oxadiazole is a biologically active nucleus which shows a broad spectrum of pharmacological activities such as antimicrobial [12], antiprotozoal [13], anti-inflammatory [14], anti-tubercular [15] etc. Thus, the combination of two biological active moieties enhances the biological activities of the novel template.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Tetrazole Regioisomers of Biphenyl as ACE Inhibitors

Meti¹,

Kamble²,

Kumbar³

et al. 2017

MOCR

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Abstract. Novel angiotensin converting enzyme (ACE) inhibitors were designed based on the structure of commercially available sartans and synthesized by N-alkylation of 5-substituted-1H-tetrazole with 4'-(bromomethyl)-biphenyl-2-carbonitrile gave 1,5-and 2,5-regioisomers of tetrazole. The nitrile group appended to biphenyl nucleus was converted into tetrazole and later the tetrazole was ring transformed into 1,3,4-oxadiazole. The synthesized compounds were screened for the ACE inhibition and some of the compounds exhibited significant results.Keywords: Biphenyl, tetrazole, N-alkylation, regioisomers, 1,3,4-Oxadiazole, ring transformation, ACE inhibition IntroductionAll the cardiovascular diseases in the present era are caused mainly by "lifestyle disorder", a term coined to redefine hypertension. Although the causes of cardiovascular disease are many, hypertension stands to be the crucial one. A recent study suggests that hypertensive patients are more prone to develop type II diabetes [1]. Thus, these chronic diseases coexist, with increasing risk of coronary artery disease, kidney damage, vision problems, enlarging of heart, stroke and heart failure. Many drugs have been developed to treat such chronic diseases with reduced risk of side effects. Thus, the efficacy of hypertensive medications involves many etiologies and disease mechanisms to treat the hypertensive related chronic disease [2]. The first line therapy for the treatment of hypertension is angiotensin converting enzyme (ACE) inhibitors and angiotensin II receptor blockers. The biphenyl-tetrazole is the key substrate [3][4][5], which belongs to a group of angiotensin II-receptor antagonists generally referred to as "sartans". These include Losartan, Valsartan and Candesartan which are useful in the treatment of hypertension, heart diseases, and bladder diseases and work by blocking the action of angiotensin II on its receptor ( Figure 1). Tetrazole is a heterocyclic moiety that functions as a carboxylic acid bioisostere with greater metabolic stability. It forms two hydrogen bonds with peptide residues in a biological target site which facilitates the binding interaction [6]. The negative charge of the tetrazolic anion is delocalized over all four nitrogens which play a major role in the clog P value and thus resulting in better oral bioavailability and cell penetration. It also exhibits many biological activities like antihypertensive [7,8], anti-inflammatory [9], endocannabinoid metabolism inhibitor, antibiotic [10] and anticonvulsant [11]. 1,3,4-Oxadiazole is a biologically active nucleus which shows a broad spectrum of pharmacological activities such as antimicrobial [12], antiprotozoal [13], anti-inflammatory [14], anti-tubercular [15] etc. Thus, the combination of two biological active moieties enhances the biological activities of the novel template.Considering all the above observations, we intended to synthesize novel scaffolds by N-alkylation of 5-substituted-1H-tetrazole 2a-d with 4'-(bromomethyl)-biphenyl-2-carbonitrile 1, there by aff...

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ChemInform Abstract: Synthesis of 2,5‐Disubstituted 1,3,4‐Oxadiazoles as Biologically Active Heterocycles.

Abstract: Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles as Biologically Active Heterocycles.-Some of the new compounds such as (VIa), (VIIIc), and (IXb) display antimicrobial and antitubercular activity.-(KAGTHARA, PREETI R.; SHAH, NIRAJ S.; DOSHI, RAJEEV K.; PAREKH, H. H.; Indian J.

Cited by 20 publications

References 0 publications

Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

2-Azetidinone – A new profile of various pharmacological activities

Synthesis of Tetrazole Regioisomers of Biphenyl as ACE Inhibitors

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