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 / 67卷 / 3期

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

页码：1065 / 1076

页数：12

共 50 条

[21] An investigation of the molecular mechanism, chemoselectivity and regioselectivity of cycloaddition reaction between acetonitrile N-Oxide and 2,5-dimethyl-2H-[1,2,3]diazaphosphole: a MEDT study
Abdellah Zeroual
Mar Ríos-Gutiérrez
Mohammed Salah
Habib El Alaoui El Abdallaoui
Luis Ramon Domingo
Journal of Chemical Sciences, 2019, 131
[22] An investigation of the molecular mechanism, chemoselectivity and regioselectivity of cycloaddition reaction between acetonitrile N-Oxide and 2,5-dimethyl-2H-[1,2,3]diazaphosphole: a MEDT study
Zeroual, Abdellah
Rios-Gutierrez, Mar
Salah, Mohammed
El Abdallaoui, Habib El Alaoui
Ramon Domingo, Luis
JOURNAL OF CHEMICAL SCIENCES, 2019, 131 (08)
[23] Computational study of the binding mechanism between farnesoid X receptor α and antagonist N-benzyl-N-(3-(tertbutyl)-4-hydroxyphenyl)-2,6-dichloro-4-(dimethylamino) benzamide
Du, Juan
Qiu, Miaoxue
Guo, Lizhong
Yao, Xiaojun
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 2019, 37 (06): : 1628 - 1640
[24] Novel Synthetic Coumarin-Chalcone Derivative (E)-3-(3-(4-(Dimethylamino)Phenyl)Acryloyl)-4-Hydroxy-2 H -Chromen-2-One Activates CREB-Mediated Neuroprotection in A β and Tau Cell Models of Alzheimer's Disease
Chiu Y.-J.
Lin T.-H.
Chen C.-M.
Lin C.-H.
Teng Y.-S.
Lin C.-Y.
Sun Y.-C.
Hsieh-Li H.M.
Su M.-T.
Lee-Chen G.-J.
Lin W.
Chang K.-H.
Lee-Chen, Guey-Jen (t43019@ntnu.edu.tw); Chang, Kuo-Hsuan (gophy5128@cgmh.org.tw); Lin, Wenwei (wenweilin@ntnu.edu.tw), 1600, Hindawi Limited (2021):
[25] Synthesis, anticancer activity and molecular docking study of (E)-4-(3,4Dichlorophenyl)-2-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)-3,4- dihydronaphthalen-1(2H)-one derivatives
Sadanandam, Kudikala
Pinnoju, Prasad
Manasa, S. K.
Sarasija, Madderla
CHEMICAL BIOLOGY LETTERS, 2024, 11 (01):
[26] STUDY OF THE REACTION BETWEEN 5-AMINO-2,4-DIHYDRO-4-[(PHENYLAMINO)METHYLENE]-2-PHENYL-3H-PYRAZOL-3-ONE AND ETHYL OXOBUTANOATE
MAQUESTIAU, A
VANDENEYNDE, JJ
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1986, 95 (03): : 189 - 195
[27] Synthesis, spectroscopy, crystal structure, TGA/DTA study, DFT and molecular docking investigations of (E)-4-(4-methylbenzyl)-6-styrylpyridazin-3(2H)-one
El Kalai, Fouad
Cinar, Emine Berrin
Lai, Chin-Hung
Daoui, Said
Chelfi, Tarik
Allali, Mustapha
Dege, Necmi
Karrouchi, Khalid
Benchat, Noureddine
JOURNAL OF MOLECULAR STRUCTURE, 2021, 1228
[28] (E)-N-Aryl-2-oxo-2-(3,4,5-trimethoxyphenyl) acetohydrazonoyl cyanides as tubulin polymerization inhibitors: Structure-based bioisosterism design, synthesis, biological evaluation, molecular docking and in silico ADME prediction
Wang, Guangcheng
Peng, Zhiyun
Peng, Shanshan
Qiu, Jie
Li, Yongjun
Lan, Yanyu
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2018, 28 (20) : 3350 - 3355
[29] Selectivity and molecular mechanism of the Au(III)-catalyzed [3+2] cycloaddition reaction between (Z)-C,N-diphenylnitrone and nitroethene in the light of the molecular electron density theory computational study
Wróblewska, Aneta
Sadowski, Mikolaj
Jasiński, Radomir
Chemistry of Heterocyclic Compounds, 2024, 60 (11) : 639 - 645
[30] Synthesis, crystallographic and spectroscopic investigation, chemical reactivity, hyperpolarizabilities and in silico molecular docking study of (Z)-2N-(tert-butylimino)-3N′-(4-methoxyphenyl) thiazolidin-4-one
Boudjenane, Fatima Zohra
Triki-Baara, Fayssal
Boukabcha, Nourdine
Belkafouf, Nour El Houda
Dege, Necmi
Saidj, Merzouk
Khelloul, Nawel
Djafri, Ayada
Chouaih, Abdelkader
JOURNAL OF MOLECULAR STRUCTURE, 2023, 1287

← 1 2 3 4 5 →