Practical synthesis, anticonvulsant, and antimicrobial activity of N-allyl and N-propargyl di(indolyl)indolin-2-ones

作者: Chandrasekaran Praveen , Asairajan Ayyanar , Paramasivan Thirumalai Perumal

DOI: 10.1016/J.BMCL.2011.04.117

关键词:

摘要: An operation friendly protocol for the synthesis of novel di(indolyl)indolin-2-ones via Cu(OTf)(2) catalyzed bis-addition N-allyl and N-propargyl indole with isatin was developed. This methodology allowed us to achieve products in excellent yields without requiring purification technique like column chromatography. All synthesized compounds were evaluated their vivo anticonvulsant activity against maximal electroshock test. Six showed maximum compared standard drug phenytoin. The scope new molecules as antimicrobial agents tested two bacterial strains (Staphylococcus aureus Escherichia coli) one fungal strain (Candida albicans).

参考文章(42)
Douglas A. Klumpp, Ka Yeun Yeung, G. K. Surya Prakash, George A. Olah, Preparation of 3,3-Diaryloxindoles by Superacid-Induced Condensations of Isatins and Aromatics with a Combinatorial Approach Journal of Organic Chemistry. ,vol. 63, pp. 4481- 4484 ,(1998) , 10.1021/JO980588G
Anne Thiry, Jean-Michel Dogne, Claudiu Supuran, Bernard Masereel, Carbonic Anhydrase Inhibitors as Anticonvulsant Agents Current Topics in Medicinal Chemistry. ,vol. 7, pp. 855- 864 ,(2007) , 10.2174/156802607780636726
Carlos C. Fortes, Clevia F.D. Garrote, SYNTHESIS OF 2-ACETYLENIC CARBOXYLIC ACIDS, 1-SULFINYL AND 1-SULFONYL-2-KETONES FROM 2-ACETYLENIC PHENYL SULFIDES Synthetic Communications. ,vol. 27, pp. 2993- 3026 ,(1997) , 10.1080/00397919708005006
P. Yogeeswari, J. Ragavendran, R. Thirumurugan, A. Saxena, D. Sriram, Ion channels as important targets for antiepileptic drug design. Current Drug Targets. ,vol. 5, pp. 589- 602 ,(2004) , 10.2174/1389450043345227
P. Yogeeswari, D. Sriram, J. Vaigundaragavendran, The GABA Shunt: An Attractive and Potential Therapeutic Target in the Treatment of Epileptic Disorders Current Drug Metabolism. ,vol. 6, pp. 127- 139 ,(2005) , 10.2174/1389200053586073
Yasushi Nishihara, Masanori Okamoto, Yoshiaki Inoue, Mikihiro Miyazaki, Mitsuru Miyasaka, Kentaro Takagi, Synthesis of symmetrical 1,3-butadiynes by homocoupling reactions of alkynylboronates mediated by a copper salt Tetrahedron Letters. ,vol. 46, pp. 8661- 8664 ,(2005) , 10.1016/J.TETLET.2005.10.056
Katsuji Ito, Shuuichiro Eno, Bunnai Saito, Tsutomu Katsuki, Enantioselective conjugate addition of diethylzinc to acyclic enones using a copper phosphino-phenol complex as catalyst Tetrahedron Letters. ,vol. 46, pp. 3981- 3985 ,(2005) , 10.1016/J.TETLET.2005.04.036
Giorgio Abbiati, Valentina Canevari, Solange Caimi, Elisabetta Rossi, Domino addition/annulation of δ-alkynylaldehydes and oxygen nucleophiles: a new entry to [1,4]oxazino[4,3-a]indoles Tetrahedron Letters. ,vol. 46, pp. 7117- 7120 ,(2005) , 10.1016/J.TETLET.2005.08.102
Javad Azizian, Ali A. Mohammadi, Ali R. Karimi, Mohammad R. Mohammadizadeh, KAl(SO4)2.12H2O as a recyclable Lewis acid catalyst for synthesis of some new oxindoles in aqueous media Journal of Chemical Research-s. ,vol. 2004, pp. 424- 426 ,(2004) , 10.3184/0308234041423600