Synthesis of benzosuberone-tethered spirooxindoles: 1-3-dipolar cycloaddition of azomethine ylides and arylidene benzosuberones

被引：5

作者：

Kumar, Sundaravel Vivek ^{[1
]}

Rani, Gandhi Uma ^{[1
]}

Divyalakshmi, Manohar ^{[1
]}

Bhuvanesh, Nattamai ^{[2
]}

Muthusubramanian, Shanmugam ^{[1
]}

Perumal, Subbu ^{[1
]}

机构：

[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India

[2] Texas A&M Univ, Dept Chem, Xray Diffract Lab, College Stn, TX 77843 USA

来源：

MOLECULAR DIVERSITY | 2019年 / 23卷 / 03期

关键词：

1,3-Dipolar cycloaddition; Azomethine ylide; Benzosuberone; Spirooxindoles; Regioselectivity; Stereoselectivity; STEREOSELECTIVE-SYNTHESIS; BIOLOGICAL EVALUATION; SPIRO-OXINDOLES; DERIVATIVES; POTENT; DISCOVERY; COLCHICINE; DESIGN;

D O I：

10.1007/s11030-018-9901-9

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：

Expedient synthesis of benzosuberone-tethered spirooxindoles was accomplished by a three-component 1,3-dipolar cycloaddition reaction between azomethine ylide (generated in situ) and arylidene benzosuberone. This protocol offers good yield and wide functional group tolerance under mild reaction condition with high regio- and stereoselectivities. [GRAPHICS] .

引用

页码：669 / 680

页数：12

共 37 条

[1] Amino-benzosuberone: A novel warhead for selective inhibition of human aminopeptidase-N/CD13 [J].

Albrecht, Sebastien ;

Al-Lakkis-Wehbe, Mira ;

Orsini, Alban ;

Defoin, Albert ;

Pale, Patrick ;

Salomon, Emmanuel ;

Tarnus, Celine ;

Weibel, Jean-Marc .

BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (04) :1434-1449

[2] Multicomponent 1,3-Dipolar Cycloaddition Reactions in the Construction of Hybrid Spiroheterocycles [J].

Arumugam, Natarajan ;

Kumar, Raju Suresh ;

Almansour, Abdulrahman I. ;

Perumal, Subbu .

CURRENT ORGANIC CHEMISTRY, 2013, 17 (18) :1929-1956

[3] Biological evaluation of benzosuberones [J].

Behbehani, Haider ;

Dawood, Kamal M. ;

Farghaly, Thoraya A. .

EXPERT OPINION ON THERAPEUTIC PATENTS, 2018, 28 (01) :5-29

[4] Ultrasound-assisted regio- and stereoselective synthesis of bis-[1′,4′-diaryl-1-oxo-spiro-benzosuberane-2,5′-pyrazoline] derivatives via 1,3-dipolar cycloaddition [J].

Behbehani, Haider ;

Ibrahim, Hamada Mohamed ;

Dawood, Kamal M. .

RSC ADVANCES, 2015, 5 (33) :25642-25649

[5] Anti-mitotic activity of colchicine and the structural basis for its interaction with tubulin [J].

Bhattacharyya, Bhabatarak ;

Panda, Dulal ;

Gupta, Suvroma ;

Banerjee, Mithu .

MEDICINAL RESEARCH REVIEWS, 2008, 28 (01) :155-183

[6] Structure-based design of spiro-oxindoles as potent, specific small-molecule inhibitors of the MDM2-p53 interaction [J].

Ding, Ke ;

Lu, Yipin ;

Nikolovska-Coleska, Zaneta ;

Wang, Guoping ;

Qiu, Su ;

Shangary, Sanjeev ;

Gao, Wei ;

Qin, Dongguang ;

Stuckey, Jeanne ;

Krajewski, Krzysztof ;

Roller, Peter P. ;

Wang, Shaomeng .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (12) :3432-3435

[7] Synthesis, anti-HCV, antioxidant, and peroxynitrite inhibitory activity of fused benzosuberone derivatives [J].

Farghaly, Thoraya A. ;

Hafez, Naglaa A. Abdel ;

Ragab, Eman A. ;

Awad, Hanem M. ;

Abdalla, Mohamed M. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) :492-500

[8] Diterpenes from Salvia broussonetii transformed roots and their insecticidal activity [J].

Fraga, BM ;

Díaz, CE ;

Guadaño, A ;

González-Coloma, A .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (13) :5200-5206

[9] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents [J].

Galliford, Chris V. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8748-8758

[10]

GEISSMAN TA, 1962, CHEMISTRY FLAVONO ED, P468

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