Design, synthesis, and docking studies of new 2-benzoxazolinone derivatives as anti-HIV-1 agents

Safakish, Mahdieh; Hajimahdi, Zahra; Zabihollahi, Rezvan; Aghasadeghi, Mohammad Reza; Vahabpour, Rouhoullah; Zarghi, Afshin

doi:10.1007/s00044-017-1969-8

Cited by 28 publications

(13 citation statements)

References 23 publications

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“…Initially, 1,3‐benzoxazol‐2‐one ( 1 ) compound was synthesized from the reaction of 2‐aminophenol and urea by using HCl as a catalyst. [ 32 ] Then, compound 1 was reacted with ethyl bromoacetate in ethanolic sodium ethoxide to obtain an ester derivative ( 2 ). 2‐(2‐Oxo‐1,3‐benzoxazol‐3( 2H )‐yl)acetohydrazide ( 3 ) was synthesized from the reaction of compound 2 and hydrazine hydrate.…”

Section: Resultsmentioning

confidence: 99%

“…This product was prepared by treating 2-amino phenol and urea in concentrated HCl for 4 hours as reported earlier. [32] Yield: 1.24 g, 92%; m.p. : 135 C-136 C, (135 C [32] ).…”

Section: Discussionmentioning

confidence: 99%

“…This product was synthesized according to the literature. [32] Yield: 1.90 g, 86%; m.p. : 90 C-91 C, (89 C [32] ).…”

Section: Synthesis Of Ethyl (2-oxo-13-benzoxazol-3(2h)-yl)acetate (2)mentioning

confidence: 99%

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Synthesis and biological evaluation of some 1,3‐benzoxazol‐2(3H)‐one hybrid molecules as potential antioxidant and urease inhibitors

Yılmaz

Menteşe

Sökmen

2020

Journal of Heterocyclic Chem

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A new series of 1,3‐benzoxazol‐2(3H)‐one hybrid compounds, including coumarin, isatin 1,3,4‐triazole and 1,3,4‐thiadiazole moieties, were synthesized and biologically evaluated for their antioxidant capacities and anti‐urease properties. The synthesized benzoxazole‐coumarin (6a–e) and benzoxazole‐isatin (10a–c) hybrids showed remarkable urease inhibitory activities with IC50 (μM), ranging from 0.0306 ± 0.0030 to 0.0402 ± 0.0030, while IC50 of standard thiourea is 0.5027 ± 0.0293. The synthesized benzoxazole‐triazole (8a–c) and benzoxazole‐thiadiazole (9a–c) hybrids showed similar urease inhibitory activities with IC50 (μM), ranging from 0.3861 ± 0.0379 to 0.5126 ± 0.0345. The antioxidant activity of the synthesized compounds was evaluated for their antioxidant activities, such as reducing power and ABTS (2,2′‐azino‐bis(3‐ethylbenzothiazoline‐6‐sulphonic acid) diammonium salt) radical scavenging. The results of ABTS radical scavenging activities of some of the synthesized molecules showed higher activities than standard Trolox, SC50 (μM) = 213.04 ± 18.12. One benzoxazole‐coumarin (6f), two benzoxazole‐isothiocyanate (7b, 7c), and two benzoxazole‐triazole (8b, 8c) derivatives showed higher activities (SC50 (μM) values, 82.07 ± 10.34, 120.19 ± 7.30, 104.58 ± 10.55, 153.26 ± 7.14, and 144.82 ± 10.68, respectively) than standard Trolox, (SC50 (μM) = 213.04 ± 18.12).

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Section: Resultsmentioning

confidence: 99%

“…This product was prepared by treating 2-amino phenol and urea in concentrated HCl for 4 hours as reported earlier. [32] Yield: 1.24 g, 92%; m.p. : 135 C-136 C, (135 C [32] ).…”

Section: Discussionmentioning

confidence: 99%

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Synthesis and biological evaluation of some 1,3‐benzoxazol‐2(3H)‐one hybrid molecules as potential antioxidant and urease inhibitors

Yılmaz

Menteşe

Sökmen

2020

Journal of Heterocyclic Chem

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“…It is estimated that 36.9 million people (including 2.6 million children) were living with HIV infection in the year 2014 according to UNAIDS-2015 report, and 1.2 million people died due to HIV as well as related diseases (Chander et al, 2016). To circumvent this challenge, there is an urgent need to discover and develop safe, green, efficient, selective and novel anti-HIV inhibitors having significant potency against drugresistant RT viral strains as well as less toxicity (Chander et al, 2016;Huang et al, 2007;Polanski et al, 2006;Safakish et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

Discovery of N-arylsulfonyl-3-acylindole benzoyl hydrazone derivatives as anti-HIV-1 agents

Che

Tian

Liu

et al. 2018

Braz. J. Pharm. Sci.

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The discovery and development of novel inhibitors with activity against variants of human immunodeficiency virus type 1 (HIV-1) is pivotal for overcoming treatment failure. As our ongoing work on research of anti-HIV-1 inhibitors, 32 N-arylsulfonyl-3-acylindole benzoyl hydrazone derivatives were prepared by introduction of the hydrazone fragments on the N-arylsulfonyl-3-acylindolyl skeleton and preliminarily screened in vitro as HIV-1 inhibitors for the first time. Among of all the reported analogues, eight compounds exhibited significant anti-HIV-1 activity, especially N-(3-nitro)phenylsulfonyl-3acetylindole benzoyl hydrazone (18) and N-(3-nitro)phenylsulfonyl-3-acetyl-6-methylindole benzoyl hydrazone (23) displayed the most potent anti-HIV-1 activity with EC 50 values of 0.26 and 0.31 μg/mL, and TI values of >769.23 and >645.16, respectively. It is noteworthy that introduction of R 3 as the methyl group and R 2 as the hydrogen group could result in more potent compounds. This suggested that introduction of R 3 as the methyl group could be taken into account for further preparation of these kinds of compounds as anti-HIV-1 agents.

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“…It is estimated that 36.9 million people (including 2.6 million children) were living with HIV infection in the year 2014 according to UNAIDS -2015 report, and 1.2 million people died due to HIV as well as related diseases [ 8 ]. To circumvent this challenge, it is urgent to discover and develop safe, green, efficient, selective, and novel anti-HIV inhibitors having significant potency against drug-resistant RT viral strains as well as less toxicity [ 8 , 9 , 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Expeditious Synthesis of 2-Alkyl-2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-aryl-1,3,4-oxadiazolines Catalyzed by HgCl2 under Solvent-Free Conditions as Potential Anti-HIV-1 Agents

et al. 2018

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A series of 2-alkyl-2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-aryl-1,3,4-oxadiazolines were expeditious prepared under microwave-assisted, catalyzed by HgCl2 and solvent-free conditions. This method has the advantage of low catalyst loading and recovering catalyst, ease reaction and repaid reaction times, easy separation products and excellent yields, and more conducive to the large-scale synthesis products. Furthermore, compounds 3s, 3y, 3a′, 3b′, 3f′, 3i′, 3q′, and 3r′ exhibited more potent anti-HIV-1 activity with EC50 values of 3.35, 6.12, 3.63, 9.54, 1.79, 0.51, 3.00, and 4.01 μg/mL, and TI values of 32.66, >32.68, 31.22, 13.94, 24.27, 39.59, 26.01, and 24.51, respectively. Especially compound 3i′ displayed the highest anti-HIV-1 activity with TI values of 39.59.

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Design, synthesis, and docking studies of new 2-benzoxazolinone derivatives as anti-HIV-1 agents

Cited by 28 publications

References 23 publications

Synthesis and biological evaluation of some 1,3‐benzoxazol‐2(3H)‐one hybrid molecules as potential antioxidant and urease inhibitors

Synthesis and biological evaluation of some 1,3‐benzoxazol‐2(3H)‐one hybrid molecules as potential antioxidant and urease inhibitors

Discovery of N-arylsulfonyl-3-acylindole benzoyl hydrazone derivatives as anti-HIV-1 agents

Microwave-Assisted Expeditious Synthesis of 2-Alkyl-2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-aryl-1,3,4-oxadiazolines Catalyzed by HgCl2 under Solvent-Free Conditions as Potential Anti-HIV-1 Agents

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