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.
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页数：11
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