AChE inhibitor: A regio- and stereo-selective 1,3-dipolar cycloaddition for the synthesis of novel substituted 5,6-dimethoxy spiro[5.3′]-oxindole-spiro-[6.3"]-2,3-dihydro-1H-inden-1"-one-7-(substituted aryl)-tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole

被引：49

作者：

Ali, Mohamed Ashraf ^{[1
]}

Ismail, Rusli ^{[1
]}

Choon, Tan Soo ^{[1
]}

Kumar, Raju Suresh ^{[2
]}

Osman, Hasnah ^{[2
]}

Arumugam, Natarajan ^{[3
]}

Almansour, Abdulrahman I. ^{[3
]}

Elumalai, Karthikeyan ^{[5
]}

Singh, Abhimanyu ^{[4
]}

机构：

[1] Univ Sains Malaysia, Inst Res Mol Med, Minden 11800, Penang, Malaysia

[2] Univ Sains Malaysia, Sch Chem Sci, Minden 11800, Penang, Malaysia

[3] King Saud Univ, Dept Chem, Coll Sci, Riyadh 11451, Saudi Arabia

[4] Alwar Pharm Coll, Dept Med Chem, Alwar 301030, Rajasthan, India

[5] Sunrise Univ, Fac Pharm, Dept Drug Discovery Res, Alwar 301030, Rajasthan, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 01期

关键词：

Alzheimer diseases; Acetyl cholinesterase; AchE inhibitor; 1,3-Dipolar cycloaddition; Azomethine ylide;

D O I：

10.1016/j.bmcl.2011.10.087

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Pyrrolothiazolyloxindole analogues share vital pharmacological properties, considered useful in Alzheimer's disease (AD). The aim of this study was synthesis and evaluate pyralothiazolyloxindole analogues if possess acetyl cholinesterase (AChE) inhibitory activity. The easily accessible one-pot synthesis of these compounds resulted to be significantly less difficult and expensive than that of donepezil. Several compounds possess anti-cholinesterase activity in the order of micro and sub-micromolar. Particularly, compound 6a was the most potent inhibitors of the series against acetyl cholinesterase enzyme with IC50 0.11 mu mol/L. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：508 / 511

页数：4

共 49 条

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[2] Synthesis of novel 16-spiro steroids: Spiro-7′-(aryl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazolo-trans-androsterone hybrid heterocycles
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[3] Regio- and stereo-selective construction of cis-indeno[1,2-c]isoxazoles via a C-H allylation/1,3-dipolar cycloaddition cascade
Zhu, Man
Zhang, Yanan
Tian, Miaomiao
Li, Xingwei
Liu, Bingxian
Chang, Junbiao
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (21): : 5879 - 5884
[4] Regio- and stereo-selective construction of cis-indeno[1,2-c]isoxazoles via a C-H allylation/1,3-dipolar cycloaddition cascade
Zhu, Man
Zhang, Yanan
Tian, Miaomiao
Li, Xingwei
Liu, Bingxian
Chang, Junbiao
Organic Chemistry Frontiers, 2022, 9 (21) : 5879 - 5884
[5] Synthesis of phosphodiesterase IVb inhibitors 2. Stereoselective synthesis of hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one and tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one derivatives
Zhmurov, P. A.
Tabolin, A. A.
Sukhorukov, A. Yu.
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Khomutova, Yu. A.
Ioffe, S. L.
Tartakovsky, V. A.
RUSSIAN CHEMICAL BULLETIN, 2011, 60 (11) : 2390 - 2395
[6] Synthesis of phosphodiesterase IVb inhibitors 2. Stereoselective synthesis of hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one and tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one derivatives
P. A. Zhmurov
A. A. Tabolin
A. Yu. Sukhorukov
A. V. Lesiv
M. S. Klenov
Yu. A. Khomutova
S. L. Ioffe
V. A. Tartakovsky
Russian Chemical Bulletin, 2011, 60 : 2390 - 2395
[7] REGIO- AND STEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION OF C-ARYL-N-PHENYLNITRONES OVER (E)-ARYLIDENE-(2H)-INDAN-1-ONES: SYNTHESIS OF HIGHLY SUBSTITUTED NOVEL SPIRO-ISOKAZOLIDINES
Wannassi, Nadia
Rammah, Mohamed Mehdi
Boudriga, Sarra
Rammah, Mohamed El Baker
Monnier-Jobe, Karin
Ciamala, Kabula
Knorr, Michael
Enescu, Mironel
Rousselin, Yoann
Kubicki, Marek M.
HETEROCYCLES, 2010, 81 (12) : 2749 - 2762
[8] 6 '-(1,3-Diphenyl-1H-pyrazol-4-yl)-7 '(1H-indol-3-ylcarbonyl)-2-oxo-1-(prop-2-en-1-yl)-5 ',6 ',7 '',7a '-tetrahydro-1'H-spiro[indoline-3,5 '-pyrrolo[1,2-c][1,3]thiazole]-7 '-carbonitrile
Kannan, Piskala Subburaman
Kathirvelan, Devaraj
Reddy, Boreddy Siva Rami
Govindan, Elumalai
SubbiahPandi, Arunachalathevar
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O857 - +
[9] Imposed hydrophobic interactions by NaCl: accountable attribute for the synthesis of spiro-[acenaphthylene-1,5′-pyrrolo[1,2-c]thiazole] derivatives via 1,3-dipolar cycloaddition reaction in aqueous medium
Dandia, Anshu
Parewa, Vijay
Kumari, Sukhbeer
Bansal, Sarika
Sharma, Amit
GREEN CHEMISTRY, 2016, 18 (08) : 2488 - 2499
[10] 1,3-dipolar cycloaddition of several azomethine ylides to [60]fullerene:: synthesis of derivatives of 2′,5′-dihydro-1′H-pyrrolo[3′,4′:1,2][60]fullerene
Wu, SH
Sun, WQ
Zhang, DW
Shu, LH
Wu, HM
Xu, JF
Lao, XF
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