Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol

被引：15

作者：

Arumugam, Natarajan ^{[1
]}

Almansour, Abdulrahman I. ^{[1
]}

Kumar, Raju Suresh ^{[1
]}

Al-thamili, Dhaifallah M. ^{[1
]}

Periyasami, Govindasami ^{[1
]}

Periasamy, V. S. ^{[2
]}

Athinarayanan, Jegan ^{[2
]}

Alshatwi, Ali A. ^{[2
]}

Mahalingam, S. M. ^{[3
]}

Menendez, J. Carlos ^{[4
]}

机构：

[1] King Saud Univ, Dept Chem, Coll Sci, POB 2455, Riyadh 11451, Saudi Arabia

[2] King Saud Univ, Dept Food Sci & Nutr, Coll Food & Agr Sci, Nanobiotecnol & Mol Biol Res Lab, Riyadh, Saudi Arabia

[3] Manipal Acad Higher Educ, Dept Atom & Mol Phys, MIT Campus, Manipal 576104, Karnataka, India

[4] Univ Complutense, Unidad Quim Organ & Farmaceut, Dept Quim Ciencias Farmaceut, Fac Farm, E-28040 Madrid, Spain

来源：

CHEMISTRY CENTRAL JOURNAL | 2018年 / 12卷

关键词：

Spiropyrrolidine; Piperidone; Domino reactions; Chemo divergent multicomponent reactions; Antiproliferative activity; Apoptosis induction; CHOLINESTERASE INHIBITORY-ACTIVITY; DIASTEREOSELECTIVE SYNTHESIS; EXPEDIENT REGIO; FACILE; PYRROLIZINE; PYRROLIDINE; DERIVATIVES;

D O I：

10.1186/s13065-018-0462-x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Background: Spiropyrrolidine tethered piperidone heterocyclic hybrids were synthesized with complete regio- and stereoselectively in excellent yield via a tandem three-component 1,3-dipolar cycloaddition and subsequent enamine reaction in [bmim] Br. The synthesized compounds were evaluated for their anticancer activity against FaDu hypopharyngeal tumor cells. Findings: Interestingly, most compounds displayed cytotoxicities similar to the standard anticancer agent bleomycin, with two of them (5a and 5g) being slightly more active than the reference drug. Conclusion: Synthesized compounds have also been evaluated for their apoptosis-inducing properties in a cancer cell model, finding that treatment with compounds 5a-e led to apoptotic cell death.

引用

页数：11

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