Synthesis, molecular docking and biological evaluation of 2-(thiophen-2-yl)-1H-indoles as potent HIV-1 non-nucleoside reverse transcriptase inhibitors

El‐Hussieny, Marwa; El‐Sayed, Naglaa F.; Ewies, Ewies F.; Ibrahim, Nabila M.; Mahran, M. R.; Fouad, Marwa A.

doi:10.1016/j.bioorg.2019.103521

Cited by 16 publications

(9 citation statements)

References 44 publications

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“…Highly substituted chromone derivatives 4a-h and 5a-h were synthesized via a one-pot, four-component reaction of aniline, furochromone carbaldehyde 1, acid derivatives 3a-d, namely, benzoic acid/or 4-amino-, 4nitrobenzoic acid/or nicotinic acid, and phenyl isocyanate/ or cyclohexyl isocyanate (Scheme 1). e structures of 4a-h were elucidated from their elemental and spectroscopic analyses (IR, 1 H NMR, and 13 C NMR) together with mass spectra which prove the structures via getting molecular ion peaks at appropriate m/z values. 1 H NMR spectra of 4a as example revealed characteristic doublet peaks for furan ring protons at δ � 6.22, 6.60 ppm, while aromatic protons appeared at 7.00-7.31 ppm as multiples.…”

Section: Resultsmentioning

confidence: 99%

“…1 H NMR spectra of 4a as example revealed characteristic doublet peaks for furan ring protons at δ � 6.22, 6.60 ppm, while aromatic protons appeared at 7.00-7.31 ppm as multiples. 13 C NMR spectrum of 4a showed 26 distinct resonances characteristic for carbon atoms 55.0 (OCH 3 ), 54.5 (OCH 3 ), 176.2 (CO), and 173.7 (CO) ppm. IR spectra of 4a-h showed disappearance of the aldehydic group.…”

Section: Resultsmentioning

confidence: 99%

“…1 H NMR (500 MHz, DMSO-d 6 ): δ � 3.99, 4.00 (s, 6H, 2OCH 3 ); 6.22, 6.60 (dd, 2H, J � 2.01 Hz, furan ring), 7.10 (s, 1H, H 7 ), 7.00-7.31 (m, 15H, CH arom) ppm. 13…”

Section: N-(49-dimethoxy-5-oxo-5h-furo[32-g]chromen-6-yl) (Phenylimino)mentioning

confidence: 99%

“…In point of this view, heterocyclic organic compounds play an important and vital role in synthesis and preparation of novel pharmacological compounds that may have a good manner in treatment of various types of tumors [12] and the human immunodeficiency virus (HIV) [13]. Our initial studies focused on the chromone and its derivatives which are important class of heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

“…H-NMR (100 MHz, DMSO-d 6 ): δ, 3.97 (s, 6H, 2OCH 3 ); 6.78, 6.52 (dd, 2H, J�2.01 Hz, furan ring); 7.00 (s, 1H, H 7 ) and 7.31-7.11 (m, 15H, CH arom.) 13. C NMR (100 MHz, DMSO-d 6 ): δ, 174.7 (CO), 158.6, 152.7, 149.8, 147.5, 146.0, 136.9, 137.1 133.1, 132.1, 129.7, 129.2, 128..97 (s, 6H, 2OCH 3 ); 6.78, 6.52 (dd, 2H, J�2.01 Hz, furan ring); 7.00 (s, 1H, H 7 ) and 7.31-7.11 (m, 14H, CH arom.).…”

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confidence: 99%

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One-Pot Synthesis of Novel Furochromone and Oxazocine Derivatives as Promising Antitumor Agents with Their Molecular Docking Studies

Borik

2020

Journal of Chemistry

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One-pot efficient synthesis of novel chromone derivatives 4a–h and that of 5a–h were described in a simple method via four-component reaction between furochromone carbaldehyde, amine, isocyanate derivatives, and benzoic acid derivatives or nicotinic acid, respectively. Also, oxazocine derivatives 7a, b were prepared via reaction of visnagine carbaldehyde, ethyl acetoacetate and isocyanate derivatives 2a, b. The obtained derivatives of novel furochromone and oxazocine derivatives were evaluated as promising antitumor agents against panel of two human cell lines, hepatocellular carcinoma (HEPG2) and breast carcinoma (MCF7). The antitumor results suggested that furochromone derivatives 5a–h have activity against MCF7 in comparison with doxorubicin as the standard drug. Furthermore, the molecular docking studies of these novel derivatives of furochromone and oxazocine showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was investigate.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…1 H NMR (500 MHz, DMSO-d 6 ): δ � 3.99, 4.00 (s, 6H, 2OCH 3 ); 6.22, 6.60 (dd, 2H, J � 2.01 Hz, furan ring), 7.10 (s, 1H, H 7 ), 7.00-7.31 (m, 15H, CH arom) ppm. 13…”

Section: N-(49-dimethoxy-5-oxo-5h-furo[32-g]chromen-6-yl) (Phenylimino)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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One-Pot Synthesis of Novel Furochromone and Oxazocine Derivatives as Promising Antitumor Agents with Their Molecular Docking Studies

Borik

2020

Journal of Chemistry

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The antimalarial activity of indole alkaloids and hybrids

Sun

et al. 2020

Archiv der Pharmazie

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Malaria, caused by the genus Plasmodium, remains a global public health concern. It is estimated by the World Health Organization that over 40% of the world's population lives in areas at risk for malarial transmission, and around half a million people succumb to this infectious disease annually, which is related to the rapid spread of drug-resistant parasite strains. Indole derivatives, which possess broadspectrum pharmacological properties, play a crucial role in the discovery of new drugs. Many indole derivatives exhibited potential in vitro and in vivo activity against both drug-sensitive and drug-resistant malaria, suggesting that the indole moiety is a useful template for the development of novel antimalarial agents.

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Design, synthesis, biological evaluation, and molecular docking of new benzofuran and indole derivatives as tubulin polymerization inhibitors

El‐Sayed

El‐Hussieny

Ewies

et al. 2021

Drug Development Research

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Microtubules and the mitotic spindle have become an important target for cancer treatment due to their critical role in cell division. In this work, a novel series of benzofuran and indole derivatives were designed and synthesized, to be evaluated as tubulin polymerization inhibitors. 2‐Acetylbenzofuran derivatives 1a,b and 3‐acetylindole 1c were condensed with Wittig reagents 2a–d and Wittig‐Horner reagents 3a–e to afford the respective 2‐ethylidene derivatives 5a–j and 7a–e. Also, iminomethylene triphenylphosphine (2e) reacted with 1a,b to afford benzofuran‐2‐ylethylidene aniline derivatives 6a,b. In addition, compounds 1a,b reacted with trialkylphosphites 4a–c to give 1:1 adduct for which the Oxaphospholo[4,3‐b]benzofuran‐7‐yl)diazene derivatives 8a–f, were assigned. The possible reactions mechanisms were discussed and structural reasoning for the new compounds were based upon spectroscopic data. Their antiproliferative activities against two cell lines namely, HepG2 and MCF7 cells were then evaluated. It was found that the benzofuran compounds 5b, 6a, and 8c exhibited the strongest antiproliferative activities against both cell lines compared to doxorubicin. By studying the mechanism of action, compound 6a showed good inhibition of tubulin polymerization which leads to mitotic spindle formation disruption, cell cycle arrest in the G2/M phase, and apoptosis of HepG2 cells. A conducted docking study confirmed the in vitro results indicating that compound 6a fitted properly at the colchicine binding site of tubulin. Based on these findings, compound 6a can be considered as a promising anticancer candidate that can be subjected for further development as a tubulin polymerization inhibitor for treating liver and breast cell carcinoma.

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Synthesis, molecular docking and biological evaluation of 2-(thiophen-2-yl)-1H-indoles as potent HIV-1 non-nucleoside reverse transcriptase inhibitors

Cited by 16 publications

References 44 publications

One-Pot Synthesis of Novel Furochromone and Oxazocine Derivatives as Promising Antitumor Agents with Their Molecular Docking Studies

One-Pot Synthesis of Novel Furochromone and Oxazocine Derivatives as Promising Antitumor Agents with Their Molecular Docking Studies

The antimalarial activity of indole alkaloids and hybrids

Design, synthesis, biological evaluation, and molecular docking of new benzofuran and indole derivatives as tubulin polymerization inhibitors

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