1033931-93-9Relevant articles and documents
Convenient Synthesis of 11-Substituted 11H-Indolo[3,2-c]quinolines by Sequential Chemoselective Suzuki Reaction/Double C–N Coupling
Pham, Ngo Nghia,Janke, Sophie,Salman, Ghazwan Ali,Dang, Tuan Thanh,Le, Thanh Son,Spannenberg, Anke,Ehlers, Peter,Langer, Peter
, p. 5554 - 5565 (2017)
A pathway to access 11-substituted 11H-indolo[3,2-c]quinolines is described. The protocol features a chemoselective Suzuki reaction of o-dihaloquinolines with o-bromophenylboronic acid, followed by double C–N coupling with primary amines. The molecular structure of a representative product is exemplified, and demonstrates well-defined π-stacking interactions in the molecular network.
Concise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor
Fandrick, Keith R.,Li, Wenjie,Zhang, Yongda,Tang, Wenjun,Gao, Joe,Rodriguez, Sonia,Patel, Nitinchandra D.,Reeves, Diana C.,Wu, Jiang-Ping,Sanyal, Sanjit,Gonnella, Nina,Qu, Bo,Haddad, Nizar,Lorenz, Jon C.,Sidhu, Kanwar,Wang, June,Ma, Shengli,Grinberg, Nelu,Lee, Heewon,Tsantrizos, Youla,Poupart, Marc-André,Busacca, Carl A.,Yee, Nathan K.,Lu, Bruce Z.,Senanayake, Chris H.
, p. 7144 - 7148 (2015/06/16)
Abstract A practical and efficient synthesis of a complex chiral atropisomeric HIV integrase inhibitor has been accomplished. The combination of a copper-catalyzed acylation along with the implementation of the BI-DIME ligands for a ligand-controlled Suzuki cross-coupling and an unprecedented bis(trifluoromethane)sulfonamide-catalyzed tert-butylation renders the synthesis of this complex molecule robust, safe, and economical. Furthermore, the overall synthesis was conducted in an asymmetric and diastereoselective fashion with respect to the imbedded atropisomer. Atropselective: An efficient asymmetric synthesis of an atropisomeric HIV inhibitor has been accomplished. The combination of a copper-catalyzed acylation with the implementation of BI-DIME ligands for a ligand-controlled Suzuki cross-coupling and an unprecedented bis(trifluoromethane)sulfonamide-catalyzed tert-butylation renders the synthesis of this complex molecule robust, safe, and economical.
Discovery, synthesis, and optimization of antimalarial 4(1 H)-quinolone-3-diarylethers
Nilsen, Aaron,Miley, Galen P.,Forquer, Isaac P.,Mather, Michael W.,Katneni, Kasiram,Li, Yuexin,Pou, Sovitj,Pershing, April M.,Stickles, Allison M.,Ryan, Eileen,Kelly, Jane Xu,Doggett, J. Stone,White, Karen L.,Hinrichs, David J.,Winter, Rolf W.,Charman, Susan A.,Zakharov, Lev N.,Bathurst, Ian,Burrows, Jeremy N.,Vaidya, Akhil B.,Riscoe, Michael K.
, p. 3818 - 3834 (2014/05/20)
The historical antimalarial compound endochin served as a structural lead for optimization. Endochin-like quinolones (ELQ) were prepared by a novel chemical route and assessed for in vitro activity against multidrug resistant strains of Plasmodium falciparum and against malaria infections in mice. Here we describe the pathway to discovery of a potent class of orally active antimalarial 4(1H)-quinolone-3-diarylethers. The initial prototype, ELQ-233, exhibited low nanomolar IC50 values against all tested strains including clinical isolates harboring resistance to atovaquone. ELQ-271 represented the next critical step in the iterative optimization process, as it was stable to metabolism and highly effective in vivo. Continued analoging revealed that the substitution pattern on the benzenoid ring of the quinolone core significantly influenced reactivity with the host enzyme. This finding led to the rational design of highly selective ELQs with outstanding oral efficacy against murine malaria that is superior to established antimalarials chloroquine and atovaquone.
PROCESS FOR THE PREPARATION OF AN HIV INTEGRASE INHIBITOR
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, (2012/10/18)
The present invention is directed to an improved process for the preparation of Compounds of Formula (I) or salts thereof which are useful in the treatment of HIV infection. In particular, the present invention is directed to an improved process for the preparation of (2S)-2-tert-butoxy-2-(4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)- 2-methylquinolin-3-yl)acetic acid or salt thereof which is useful in the treatment of HIV infection. R4 is selected from the group consisting of (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k), (l), (m), (n) and (o); and R6 and R7 are each independently selected from H, halo and (C1-6) alkyl.
Convenient and efficient microwave-assisted synthesis of a methyl derivative of the fused indoloquinoline alkaloid cryptosanguinolentine
Gengan, Robert M.,Pandian, Pitchai,Kumarsamy, Chandraprakash,Mohan, Palathurai S.
experimental part, p. 3171 - 3178 (2010/09/04)
An efficient synthesis of a methyl derivative of the indoloquinoline alkaloid cryptosanguinolentine based on microwave-assisted reactions is described. The microwave-assisted synthesis of an intermediate 4-hydroxy-2-methylquinoline yielded 86% of the desired product and other intermediates prepared yielded high % of products in shorter reaction times, under optimum conditions, as compared to traditional methods.
Photo induced synthesis of methyl derivative of cryptosanguinolentine
Pitchai,Mohan,Gengan
experimental part, p. 692 - 696 (2009/12/24)
A simpler method to synthesize methyl derivative of an alkaloid ciyprosanguinolentine is described. 4-Hydroxy-2- methylquinoline is iodized using iodine, potassium iodide and aqueous sodium hydroxide and dehydroxyhalogenated with phosphorous oxychloride. The respective anilinoquinoline is prepared and cyclized by UV irradiation. Upon selective methylation 5,6-dimethyl-5//-indolo[3,2-c]quinoline is produced which is utilized as a DNA intercalating agent.
