Molecular properties prediction and synthesis of novel 1,3,4-oxadiazole analogues as potent antimicrobial and antitubercular agents

Ahsan, Mohamed Jawed; Samy, Jeyabalan Govinda; Khalilullah, Habibullah; Nomani, Md. Shivli; Saraswat, Pankaj; Gaur, Ramakant; Singh, Abhimanyu

doi:10.1016/j.bmcl.2011.10.057

Cited by 167 publications

(88 citation statements)

References 21 publications

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“…Ahsan et al [55] synthesized a series of 1,5-dimethyl-2-phenyl-4-{[(5-aryl-1,3,4-oxadiazol-2-yl)methyl]amino}-1,2- Macaev et al [56] synthesized a series of 82, 5-aryl-2-thio-1,3,4-oxadiazole derivatives ( Table 2) and screened them for their anti-mycobacterial activities against Mycobacterium tuberculosis H37Rv. They further studied structure-activity relationships of the given series by using the electronic topological method combined with neural networks (ETM-NN).…”

Section: Antibacterial Antimycobecterial and Antifungal Activitiesmentioning

confidence: 98%

1,3,4-Oxadiazole: A Biologically Active Scaffold

Khalilullah

Ahsan²,

Hedaitullah³

et al. 2012

MRMC

133

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There has been considerable interest in the development of novel compounds with anticonvulsant, antidepressant, analgesic, anti-inflammatory, antiallergic, antipsychotic, antimicrobial, antimycobecterial, antitumour, antiviral and antitubercular activities. 1,3,4-oxadiazoles constitute an important class of compounds for new drug development. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. These observations led to the development of new 1,3,4-oxadiazole derivatives. This review article describes the various biological activities associated with 1,3,4-oxadiazole ring system and is useful in guiding the researchers across the world working on this moiety and consequently have been instrumental in the advancement of 1,3,4-oxadiazole chemistry.

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Section: Antibacterial Antimycobecterial and Antifungal Activitiesmentioning

confidence: 98%

1,3,4-Oxadiazole: A Biologically Active Scaffold

Khalilullah

Ahsan²,

Hedaitullah³

et al. 2012

MRMC

133

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“…The properties for drug similarity were analyzed according to Lipinski's rule of five (molecular mass of Յ500 Da, logP [logarithm of compound partition coefficient between n-octanol and water] of Յ5, H-bond donors [HBD] of Յ5, and H-bond acceptors [HBA] of Յ10) and using topological polar surface area (TPSA) values from the Molinspiration online property calculator tool kit, using the Molinspiration property calculation program (http://www.molinspiration.com /services/properties.html). TPSA was used to calculate the percentage of absorption (% Abs) according to the equation % Abs ϭ 109 Ϫ (0.345 ϫ TPSA) (19).…”

Section: Rna Extraction and Quantitative Reverse Transcription-pcr (Rmentioning

confidence: 99%

Leishmanicidal Activities of Novel Methylseleno-Imidocarbamates

Fernández-Rubio

Campbell

Vacas

et al. 2015

Antimicrob Agents Chemother

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fThe generation of new antileishmanial drugs has become a priority. Selenium and its derivatives stand out as having promising leishmanicidal activity. In fact, some parasites express selenoproteins and metabolize selenium. Recently, selenium derivatives have shown the potential to reduce parasitemia, clinical manifestations, and mortality in parasite-infected mice. In this paper, after selecting four candidates according to drug similarity parameters, we observed that two of them, called compounds 2b [methyl-N,N=-di(thien-2-ylcarbonyl)-imidoselenocarbamate] and 4b [methyl-N,N=-di(5-nitrothien-3-ylcarbonyl)-imidoselenocarbamate], exhibit low 50% inhibitory concentrations (IC 50 s) (<3 M) and good selectivity indexes (SIs) (>5) in Leishmania major promastigotes and lack toxicity on macrophages. In addition, in analysis of their therapeutic potential against L. major in vitro infection, both compounds display a dramatic reduction of amastigote burden (ϳ80%) with sublethal concentrations. Furthermore, in macrophages, these selenocompounds induce nitric oxide production, which has been described to be critical for defense against intracellular pathogens. Compounds 2b and 4b were demonstrated to cause cell cycle arrest in G 1 . Interestingly, evaluation of expression of genes related to proliferation (PCNA), treatment resistance (ABC transporter and alpha-tubulin), and virulence (quinonoid dihydropteridine reductase [QDPR]) showed several alterations in gene expression profiling. All these results prompt us to propose both compounds as candidates to treat leishmanial infections.

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“…The widespread use of 1,3,4-oxadiazoles as a scaffold in medicinal chemistry establishes this moiety as a member of the privileged structural class due to their remarkable biological and pharmacological properties, such as anticancer [4–7], antitubercular [8, 9], antibacterial [8], antifungal [10], anti-HIV [11], anti-inflammatory [12], and insecticidal [13] activities. Zibotentan, an endothelin receptor A (ET A ) antagonist, is an anticancer agent which contains 1,3,4-oxadiazole ring [14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Activity ofN-Aryl-5-substituted-1,3,4-oxadiazol-2-amine Analogues

Ahsan¹,

Sharma²,

Singh³

et al. 2014

BioMed Research International

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In continuance of our search for anticancer agents, we report herein the synthesis and anticancer activity of some novel oxadiazole analogues. The compounds were screened for anticancer activity as per National Cancer Institute (NCI US) protocol on leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers cell lines. N-(2,4-Dimethylphenyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-amine (4s) showed maximum activity with mean growth percent (GP) of 62.61 and was found to be the most sensitive on MDA-MB-435 (melanoma), K-562 (leukemia), T-47D (breast cancer), and HCT-15 (colon cancer) cell lines with GP of 15.43, 18.22, 34.27, and 39.77, respectively. Maximum GP was observed on MDA-MB-435 (melanoma) cell line (GP = 6.82) by compound N-(2,4-dimethylphenyl)-5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-amine (4u).

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Molecular properties prediction and synthesis of novel 1,3,4-oxadiazole analogues as potent antimicrobial and antitubercular agents

Cited by 167 publications

References 21 publications

1,3,4-Oxadiazole: A Biologically Active Scaffold

1,3,4-Oxadiazole: A Biologically Active Scaffold

Leishmanicidal Activities of Novel Methylseleno-Imidocarbamates

Synthesis and Anticancer Activity ofN-Aryl-5-substituted-1,3,4-oxadiazol-2-amine Analogues

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