142356-63-6Relevant articles and documents
SMALL MOLECULE REGULATORS OF STEROID RECEPTOR COACTIVATORS AND METHODS OF USE THEREOF
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Paragraph 0277; 0279; 0282; 0283; 0285, (2017/10/27)
Small molecule regulators of steroid receptor coactivator (SRC) family proteins are provided, as well as methods for their use in treating or preventing SRC-related diseases. The SRC-related diseases can include cancer, metabolic disorders, human immunodeficiency virus, neurodegenerative disorders, and/or inflammatory diseases. Also provided are methods for regulating SRC family proteins in a cell.
Design, syntheses, and structure-activity relationships of novel NPY Y5 receptor antagonists: 2-{3-Oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole derivatives
Ogino, Yoshio,Ohtake, Norikazu,Nagae, Yoshikazu,Matsuda, Kenji,Moriya, Minoru,Suga, Takuya,Ishikawa, Makoto,Kanesaka, Maki,Mitobe, Yuko,Ito, Junko,Kanno, Tetsuya,Ishihara, Akane,Iwaasa, Hisashi,Ohe, Tomoyuki,Kanatani, Akio,Fukami, Takehiro
scheme or table, p. 5010 - 5014 (2009/05/07)
Design, syntheses, and structure-activity relationships of a novel class of 2-{3-oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole NPY Y5 receptor antagonists are described. The benzimidazole structures were newly designed based on the urea linkage of our prototype Y5 receptor antagonists (2 and 3). By optimizing substituents on the benzimidazole core part of the lead compound 5a, we were able to develop a potent, orally available, and brain-penetrable Y5 selective antagonist (5k). Crown Copyright
Design, synthesis, and antiviral evaluation of 2-chloro-5,6-dihalo-1- β-D-ribofuranosylbenzimidazoles as potential agents for human cytomegalovirus infections
Zou,Drach,Townsend
, p. 811 - 818 (2007/10/03)
2-Chloro-5,6-difluorobenzimidazole (8) was prepared from 4,5-difluoro- 2-nitroaniline (5) via successive reduction, cyclization, and diazotization reactions. 2-Chloro-5,6-dibromobenzimidazole (10) was obtained by a direct bromination of 2-chlorobenzimidazole (9) with bromine-water. 2-Chloro-5,6- diiodobenzimidazele (15) was synthesized by a stepwise transformation of the nitre functions of 2-chloro-5,6-dinitrobenzimidazole (11) into iodo groups via diazotization reactions. Ribosylation of 8, 10, and 15 gave the respective β nucleosides 16a-c as the major products along with a small amount of the α anomers 17a-c. Deprotection of 16a-c afforded the corresponding free β nucleosides 2-chloro-5,6-difluoro-1-β-D- ribofuranosylbenzimidazole (2), 2-chloro-5,6-dibromo-1-β-D- ribofuranosylbenzimidazole (3), and 2-chloro-5,6-diiodo-1-β-D- ribofuranosylbenzimidazole (4). Similar deprotection of the α anomers (17a- c) resulted in a removal of the acetyl protecting groups and a concomitant cyclization to give the 2,2'-O-cyclonucleosides (18a-c). Mast of the benzimidazole heterocycles, but not the difluoro analog, were active against human cytomegalovirus (HCMV) (IC50's = 3-40 μM) and herpes simplex virus type 1 (HSV-1) (IC50's = 50-90 μM). This activity, however, was not well separated from cytotoxicity, IC50's = 10-100 μM. The corresponding unsubstituted, the 5,6-dimethyl, and the 5,6-difluoro ribonucleosides (19, 20, and 2, respectively), were inactive against both viruses. Similar to the previously reported 2,5,6-trichloro analog (TCRB), the 5,6-dibromo ribonucleoside 3 was active against HCMV (IC50 ? 4 μM) but more cytotoxic than TCRB. The 5,6-diiodo analog 4 also was active (IC50 ? 2 μM) but more cytotoxic (IC50 = 10-20 μM) than either 3 or TCRB. The cyclonucleosides were inactive against both viruses and not cytotoxic, or slightly active with corresponding cytotoxicity. The order of activity against HCMV of the dihalobenzimidazole ribonucleosides was I ? Br ? CI >> F > H = CH3. The order of cytotoxicity among the most active compounds, however, was I > Br > Cl, thereby establishing that TCRB had the best antiviral properties.
