ADME Study, Molecular Docking, Elucidating the Selectivities and the Mechanism of [4+2] Cycloaddition Reaction Between (E)-N ((dimethylamino)methylene)benzothioamide and (S)-3-acryloyl-4-phenyloxazolidin-2-one

被引：2

作者：

Atif, Mhamed ^{[1
]}

Barhoumi, Ali ^{[2
]}

Syed, Asad ^{[3
]}

Bahkali, Ali H. ^{[3
]}

Chafi, Mohammed ^{[4
]}

Tounsi, Abdessamad ^{[1
]}

Zeroual, Abdellah ^{[2
]}

Paray, Bilal Ahamad ^{[5
]}

Wang, Shifa ^{[6
]}

El Idrissi, Mohammed ^{[7
]}

机构：

[1] Sultan Moulay Slimane Univ, Fac Sci & Tech Beni Mellal, Lab Genie Environnemental Ecol & Agroind, Beni Mellal, Morocco

[2] Chouaib Doukkali Univ, Fac Sci, Mol Modelling & Spect Res Team, POB 20, El Jadida 24000, Morocco

[3] King Saud Univ, Coll Sci, Dept Bot & Microbiol, POB 2455, Riyadh 11451, Saudi Arabia

[4] Hassan II Univ Casablanca, Higher Sch Technol, LIPE, BP 8012, Oasis, Morocco

[5] King Saud Univ, Coll Sci, Dept Zool, POB 2455, Riyadh 11451, Saudi Arabia

[6] Chongqing Three Gorges Univ, Sch Elect & Informat Engn, Chongqing 404000, Peoples R China

[7] Sultan Moulay Slimane Univ, Fac Polydisciplinary, Team Chem Proc & Appl Mat, Beni Mellal, Morocco

来源：

MOLECULAR BIOTECHNOLOGY | 2024年

关键词：

MEDT; BET; ELF; 4+2] cycloaddition reaction; ELECTRON-DENSITY THEORY;

D O I：

10.1007/s12033-024-01105-w

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The molecular electron density theory (MEDT) was employed to examine the [4 + 2] cycloaddition reaction between (E)-N-((dimethylamino)methylene)benzothioamide (1) and (S)-3-acryloyl-4-phenyloxazolidin-2-one (2) at the B3LYP/6-311++G(d,p) design level. Parr functions and energy studies clearly show that this reaction is regio- and stereoselective, in perfect agreement with experimental results. By evaluating the chemical mechanism in terms of bond evolution theory (BET) and electron localization function (ELF), which divulges a variety of variations in the electron density along the reaction path, a single-step mechanism with highly asynchronous transition states structures was revealed. Additionally, we conducted a docking study on compounds P1, P2, P3, and P4 in the SARS-CoV-2 main protease (6LU7) in comparison to Nirmatrelvir. Our findings provide confirmation that product P4 may serve as a potent antiviral drug.

引用

页数：12

共 50 条

[1] On the mechanism of the Fe(CO)(5)-catalyzed Kharasch reaction .1. Stereochemistry of addition of BrCCl3 to (R)-3-(E)-cinnamoyl-4-phenyloxazolidin-2-one, (R)-3-(E)-acryloyl-4-phenyloxazolidin-2-one, and their pi-complexes with Fe(CO)(4)
Tararov, VI
Saveleva, TF
Struchkov, YT
Pisarevskii, AP
Raevskii, NI
Belokon, YN
[J]. RUSSIAN CHEMICAL BULLETIN, 1996, 45 (03) : 600 - 609
[2] DFT Study on the Molecular Mechanism of the [4+2] Cycloaddition between Thiobenzophenone and Arylalkenes via Radical Cations
Domingo, Luis R.
Perez-Ruiz, Raul
Argueello, Juan E.
Miranda, Miguel A.
[J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (19): : 5718 - 5722
[3] Elucidating the selectivities and the mechanism of [3+2] cycloloaddition reaction between 9α-hydroxyparthenolide and 4-methylbenzene-nitrile-oxide
Ouahdi, Z.
Aitouna, A. Oueld
Barhoumi, A.
Belghiti, M. E.
El Idrissi, M.
Abdellaoui, H. El Alaoui
Syed, A.
Zeroual, A.
Benharref, A.
[J]. COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2023, 1226
[4] Molecular Docking, Regio, Chemo and Stereoselectivity Study of the [3 + 2] Cycloaddition Reaction Between Pyridazi-3-one and Nitrilimine
Fatima Asserne
Zineb Ouahdi
Yassine Hakmaoui
Asli Eşme
Said Abouricha
Habib El Alaoui Abdellaoui
Asad Syed
Abdellah Zeroual
[J]. Chemistry Africa, 2024, 7 : 53 - 62
[5] Molecular Docking, Regio, Chemo and Stereoselectivity Study of the [3+2] Cycloaddition Reaction Between Pyridazi-3-one and Nitrilimine
Asserne, Fatima
Ouahdi, Zineb
Hakmaoui, Yassine
Esme, Asli
Abouricha, Said
Abdellaoui, Habib El Alaoui
Syed, Asad
Zeroual, Abdellah
[J]. CHEMISTRY AFRICA-A JOURNAL OF THE TUNISIAN CHEMICAL SOCIETY, 2024, 7 (01): : 53 - 62
[6] Correction: Molecular Docking, Regio, Chemo and Stereoselectivity Study of the [3 + 2] Cycloaddition Reaction Between Pyridazi-3-one and Nitrilimine
Fatima Asserne
Zineb Ouahdi
Yassine Hakmaoui
Asli Eşme
Said Abouricha
Habib El Alaoui Abdellaoui
Asad Syed
Abdellah Zeroual
[J]. Chemistry Africa, 2024, 7 : 621 - 621
[7] Elucidating the mechanism and selectivity of [3+2] cycloaddition: a DFT and molecular docking investigation of the reaction of 6-butoxy-5,6-dihydro-4H-1,2-oxazine 2-oxide with dimethyl maleate
Mohammad-Salim, Haydar
de Julian-Ortiz, Jesus Vicente
Dahlous, Kholood A.
Islam, Mohammad Shahidul
Almutairi, Tahani Mazyad
Benmetir, Sofiane
[J]. STRUCTURAL CHEMISTRY, 2024,
[8] Theoretical study on the reaction mechanism of CH3CH2+N(4S)
Yang, Y
Zhang, WJ
Pei, SX
Shao, J
Huang, W
Gao, XM
[J]. CHINESE JOURNAL OF CHEMICAL PHYSICS, 2005, 18 (05) : 759 - 764
[9] Molecular Docking, Regio, Chemo and Stereoselectivity Study of the [3 + 2] Cycloaddition Reaction Between Pyridazi-3-one and Nitrilimine (vol 7, pg 53, 2024)
Asserne, Fatima
Ouahdi, Zineb
Hakmaoui, Yassine
Esme, Asli
Abouricha, Said
Abdellaoui, Habib El Alaoui
Syed, Asad
Zeroual, Abdellah
[J]. CHEMISTRY AFRICA-A JOURNAL OF THE TUNISIAN CHEMICAL SOCIETY, 2024, 7 (02): : 621 - 621
[10] Ab initio study on the mechanism of the radical reaction NNH(2A′)+N(4S)→N2+NH(3Σ-)
Xu, ZF
Sun, JZ
[J]. CHEMICAL PHYSICS LETTERS, 1997, 281 (4-6) : 452 - 456

← 1 2 3 4 5 →