On December 15, 2013, Shiokawa, Zenyu; Hashimoto, Kentaro; Saito, Bunnai; Oguro, Yuya; Sumi, Hiroyuki; Yabuki, Masato; Yoshimatsu, Mie; Kosugi, Yohei; Debori, Yasuyuki; Morishita, Nao; Dougan, Douglas R.; Snell, Gyorgy P.; Yoshida, Sei; Ishikawa, Tomoyasu published an article.Name: H-Idc-OH The title of the article was Design, synthesis, and biological activities of novel hexahydropyrazino[1,2-a]indole derivatives as potent inhibitors of apoptosis (IAP) proteins antagonists with improved membrane permeability across MDR1 expressing cells. And the article contained the following:
The authors previously reported octahydropyrrolo[1,2-a]pyrazine derivative (T-3256336) as a potent antagonist for inhibitors of apoptosis (IAP) proteins. Because compound T-3256336 was susceptible to MDR1 mediated efflux, the authors developed another scaffold, hexahydropyrazino[1,2-a]indole, using structure-based drug design. The fused benzene ring of this scaffold was aimed at increasing the lipophilicity and decreasing the basicity of the scaffold to improve the membrane permeability across MDR1 expressing cells. The authors established a chiral pool synthetic route to yield the desired tricyclic chiral isomers. Chem. modification of the core scaffold led to a representative compound I, which showed strong inhibition of IAP binding (X chromosome-linked IAP [XIAP]: IC50 23 nM and cellular IAP [cIAP]: IC50 1.1 nM) and cell growth inhibition (MDA-MB-231 cells: GI50 2.8 nM) with high permeability and low potential of MDR1 substrate. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Name: H-Idc-OH
The Article related to hexahydropyrazinoindole preparation inhibitors of apoptosis iap protein antagonist, crystal structure, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1-hydroxybenzotriazole, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, ac, cdcl(3), dipea, dmf, dmso, dmt-mm, edc, et, hatu, hobt, hexahydropyrazino[1,2-a]indole and other aspects.Name: H-Idc-OH
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles