16800-67-2Relevant articles and documents
Orally Effective Aminoalkyl 10H-Indolo[3,2-b]quinoline-11-carboxamide Kills the Malaria Parasite by Inhibiting Host Hemoglobin Uptake
Mudududdla, Ramesh,Mohanakrishnan, Dinesh,Bharate, Sonali S.,Vishwakarma, Ram A.,Sahal, Dinkar,Bharate, Sandip B.
, p. 2581 - 2598 (2018)
A series of indolo[3,2-b]quinoline-C11-carboxamides were synthesized by incorporation of aminoalkyl side chains into the core of indolo[3,2-b]quinoline-C11-carboxylic acid. Their in vitro antiplasmodial evaluation against Plasmodium falciparum led to the identification of a 2-(piperidin-1-yl)ethanamine-linked analogue {2-bromo-N-[2-(piperidin-1-yl)ethyl]-10H-indolo[3,2-b]quinoline-11-carboxamide (3 g)} (IC50=1.3 μm) as the most promising compound exhibiting good selectivity indices against mammalian cell lines. The kill kinetics on erythrocytic-stage parasites revealed that 3 g caused complete killing of only the trophozoite-stage parasites. Mechanistic studies showed that 3 g targets the food vacuole of the parasite and inhibits hemoglobin uptake, β-hematin formation, and the basic endocytic processes of the parasite. Analogue 3 g was found to be orally bioavailable, and its curative antimalarial studies at 50 mg per kg p.o. against a Plasmodium berghei (ANKA)-infected mouse model revealed that mice treated with 3 g showed 27–35 % suppression of parasitemia with an increase in life span relative to untreated, control mice. Thus, the present work demonstrated a proof of concept for the oral efficacy of indolo[3,2-b]quinoline-C11-carboxamides.
A concise synthesis of the DNA-intercalating and antimalarial alkaloid cryptolepine and its fluorescence behaviour in solvents of different polarities
Lai, Tapan Kumar,Chatterjee, Asima,Banerji, Julie,Sarkar, Deboleena,Chattopadhyay, Nitin
, p. 1975 - 1983 (2008)
A microwave-induced rapid and facile synthesis of the DNA-intercalating and antimalarial drug cryptolepine is described. The key step in this synthesis involves the aqueous-phase base-catalyzed condensation of isatin and 1-acetyl-1H-indol-3-yl acetate which has been simplified and expedited by dielectric heating, employing an ordinary domestic microwave oven. The method transforms the synthesis of an important drug molecule from a prohibitively lengthy process to a matter of a few minutes with a much improved yield. Dual absorption and fluorescence is observed from the molecular system in solvents of different polarity thus providing valuable insight into its binding modes toward protein or DNA.
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Tighineanu,E. et al.
, p. 1887 - 1890 (1978)
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Construction of Oxepino[3,2-b]indoles via [4+3] Annulation of 2-Ylideneoxindoles with Crotonate-Derived Sulfur Ylides
Fei, Xing-Hai,Guan, Xiang,He, Bin,Li, Zong-Qin,Wang, Da-Peng,Yang, Fen-Fen,Yang, Yuan-Yong,Zhao, Yong-Long,Zhou, Meng
, p. 3018 - 3024 (2021/06/26)
A [4+3] annulation of 2-ylideneoxindoles with crotonate-derived sulfur ylides has been developed. A series of oxepino[3,2-b]indoles were prepared in moderate to excellent yields (62-93%) under mild conditions. Moreover, the synthetic oxepino[3,2-b] indoles can be further transformed into more complex cyclopropa[5,6]oxepino[3,2-b]indoles via a [2+1] cyclopropanation. In addition, the synthetic compounds show certain antiproliferative activity against K562 and MCF-7 cells, and its IC50 values for these two kinds of tumor cells up to 5.40±0.88 μM and 18.41±0.50 μM, respectively. (Figure presented.).