Synthesis and molecular docking of novel N-((2-chloroquinolin-3-yl) methylene)-4-methylbenzenamine derivatives as anti-HIV-1 reverse transcriptase inhibitors

被引：1
|
作者：
Fazlinezhad, Maassoumeh [1 ]
Nakhaei, Ahmad [2 ]
Eshghi, Hossein [3 ]
Saadatmandzadeh, Mohammad [3 ]
机构：
[1] Payame Noor Univ, Dept Chem, Tehran 193953697, Iran
[2] Islamic Azad Univ, Mashhad Branch, Young Researchers & Elite Club, Mashhad, Razavi Khorasan, Iran
[3] Ferdowsi Univ Mashhad, Fac Sci, Chem Dept, Mashhad, Razavi Khorasan, Iran
来源：
EURASIAN CHEMICAL COMMUNICATION | 2019年 / 1卷 / 02期
关键词：
N-((2-chloroquinolin-3-yl) methylene)-4-methylbenzenamine; mlecular docking; p-toluidine; 2-chloroquinoline-3-carbaldehyde; anti-HIV; Vilsmeier-Haack reagent;
D O I：
10.33945/SAMI/ECC.2019.2.1
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
In this research work, a proficient method has been developed for the preparation of novel N-((2-chloroquinolin-3-yl) methylene)-4-methylbenzenamine derivatives from 2-chloroquinoline-3-carbaldehyde derivatives and p-toluidine in ethanol as solvent and using catalytic amount of acetic acid under reflux conditions to obtain desired products in good yields. The identification of all the synthesized compounds was confirmed by melting point, FT-IR, H-1 NMR, and C-13 NMR. Also, in the present work, all the synthesized compounds were evaluated for their molecular docking as anti-HIV-1 reverse transcriptase inhibitors using GOLD 5.2. software. The results of molecular docking showed that all the compounds established 'pi-pi' interactions with side chain of amino acid.
引用
收藏
页码：125 / 133
页数：9
相关论文
共 50 条
  • [31] 3-Hydroxypyrimidine-2, 4-dione Derivatives as HIV Reverse Transcriptase-Associated RNase H Inhibitors: QSAR Analysis and Molecular Docking Studies
    Mostoufi, Azar
    Chamkouri, Narges
    Kordrostami, Samaneh
    Alghasibabaahmadi, Elham
    Mojaddami, Ayyub
    IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH, 2020, 19 (01): : 84 - 97
  • [32] Design, synthesis and molecular docking of pyrazolo [3,4d] thiazole hybrids as potential anti-HIV-1 NNRT inhibitors
    Kasralikar, H. M.
    Jadhavar, S. C.
    Goswami, S., V
    Kaminwar, N. S.
    Bhusare, S. R.
    BIOORGANIC CHEMISTRY, 2019, 86 : 437 - 444
  • [33] Design, synthesis, in vitro and in silico studies of novel 4-oxoquinoline ribonucleoside derivatives as HIV-1 reverse transcriptase inhibitors
    Forezi, Luana da S. M.
    Ribeiro, Mariana M. J.
    Marttorelli, Andressa
    Abrantes, Juliana L.
    Rodrigues, Carlos R.
    Castro, Helena Carla
    Souza, Thiago Moreno L.
    Boechat, Fernanda C. S.
    de Souza, Alessandra M. T.
    de Souza, Maria Cecilia B., V
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 194
  • [34] 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, Mohamed R. H.
    Fouad, Marwa A.
    BIOORGANIC CHEMISTRY, 2020, 95
  • [35] CCR5 antagonists as anti-HIV-1 agents.: Part 2:: Synthesis and biological evaluation of N-[3-(4-benzylpiperidin-1-yl)propyl]-N,N′-diphenylureas
    Imamura, S
    Kurasawa, O
    Nara, Y
    Ichikawa, T
    Nishikawa, Y
    Iida, T
    Hashiguchia, S
    Kanzaki, N
    Iizawa, Y
    Baba, M
    Sugihara, Y
    BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) : 2295 - 2306
  • [36] Docking studies of some 5-hydroxypyridine-4-one derivatives: evaluation of integrase and ribonuclease H domain of reverse transcriptase as possible targets for anti-HIV-1 activity
    Sirous, Hajar
    Zabihollahi, Rezvan
    Aghasadeghi, Mohammad R.
    Sadat, Seyed Mehdi
    Saghaie, Lotfollah
    Fassihi, Afshin
    MEDICINAL CHEMISTRY RESEARCH, 2015, 24 (05) : 2195 - 2212
  • [37] Design, Synthesis, Molecular Docking, and Antimicrobial Activity of N-{(E)-[2-(Morpholin-4-yl)quinolin-3-yl]methylidene}aniline Derivatives
    D. Subhash
    K. Bhaskar
    Russian Journal of Organic Chemistry, 2020, 56 : 498 - 503
  • [38] Docking studies of some 5-hydroxypyridine-4-one derivatives: evaluation of integrase and ribonuclease H domain of reverse transcriptase as possible targets for anti-HIV-1 activity
    Hajar Sirous
    Rezvan Zabihollahi
    Mohammad R. Aghasadeghi
    Seyed Mehdi Sadat
    Lotfollah Saghaie
    Afshin Fassihi
    Medicinal Chemistry Research, 2015, 24 : 2195 - 2212
  • [39] Design, Synthesis, Molecular Docking, and Antimicrobial Activity of N-{(E)-[2-(Morpholin-4-yl)quinolin-3-yl]methylidene}aniline Derivatives
    Subhash, D.
    Bhaskar, K.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (03) : 498 - 503
  • [40] Synthesis and anti-HIV-1 activity evaluation of 5-alkyl-2-alkylthio-6-(arylcarbonyl or α-cyanoarylmethyl)-3,4-dihydropyrimidin-4(3H)-ones as novel non-nucleoside HIV-1 reverse transcriptase inhibitors
    Ji, Lei
    Chen, Fen-Er
    De Clercq, Erik
    Balzarini, Jan
    Pannecouque, Christophe
    JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (08) : 1778 - 1786
12345