7480-36-6Relevant academic research and scientific papers
BICYCLIC UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS USEFUL FOR THE TREATMENT OF PAIN
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, (2014/06/11)
Compounds of Formula I: or stereoisomers, tautomers, or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein Ring A, Ring C and X are as defined herein, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation/inflammatory diseases, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis and pelvic pain syndrome.
Discovery of a novel class of dimeric smac mimetics as potent IAP antagonists resulting in a clinical candidate for the treatment of cancer (AZD5582)
Hennessy, Edward J.,Adam, Ammar,Aquila, Brian M.,Castriotta, Lillian M.,Cook, Donald,Hattersley, Maureen,Hird, Alexander W.,Huntington, Christopher,Kamhi, Victor M.,Laing, Naomi M.,Li, Danyang,MacIntyre, Terry,Omer, Charles A.,Oza, Vibha,Patterson, Troy,Repik, Galina,Rooney, Michael T.,Saeh, Jamal C.,Sha, Li,Vasbinder, Melissa M.,Wang, Haiyun,Whitston, David
, p. 9897 - 9919 (2014/01/17)
A series of dimeric compounds based on the AVPI motif of Smac were designed and prepared as antagonists of the inhibitor of apoptosis proteins (IAPs). Optimization of cellular potency, physical properties, and pharmacokinetic parameters led to the identification of compound 14 (AZD5582), which binds potently to the BIR3 domains of cIAP1, cIAP2, and XIAP (IC50 = 15, 21, and 15 nM, respectively). This compound causes cIAP1 degradation and induces apoptosis in the MDA-MB-231 breast cancer cell line at subnanomolar concentrations in vitro. When administered intravenously to MDA-MB-231 xenograft-bearing mice, 14 results in cIAP1 degradation and caspase-3 cleavage within tumor cells and causes substantial tumor regressions following two weekly doses of 3.0 mg/kg. Antiproliferative effects are observed with 14 in only a small subset of the over 200 cancer cell lines examined, consistent with other published IAP inhibitors. As a result of its in vitro and in vivo profile, 14 was nominated as a candidate for clinical development.
Asymmetric synthesis of chiral 1,3-diaminopropanols: Bisoxazolidine- catalyzed C-C bond formation with α-keto amides
Xu, Hanhui,Wolf, Christian
, p. 12249 - 12252 (2012/02/01)
Three high-yielding steps lead to the formation of chiral 1,3-diaminopropanols from aliphatic and aromatic α-keto amides. In this approach, a nitroaldol reaction, which is catalyzed by Cu(SO2CF 3)2 and the bisoxazolidine ligand L1, is followed by two mild reduction reactions (see scheme). Laborious protection and deprotection steps can be avoided by using this method.
Chemoenzymatic preparation of enantiopure isomers of 4-aminochroman-3-ol and 1-amino-1,2,3,4-tetrahydronaphthalen-2-ol
Recuero, Veronica,De Gonzalo, Gonzalo,Brieva, Rosario,Gotor, Vicente
, p. 4224 - 4230 (2007/10/03)
Enantiomerically pure N-protected cis-4-aminochroman-3-ol (key precursor in the synthesis of novel HIV second-generation protease inhibitors), its trans isomer and both cis- and trans-1-amino-1,2,3,4-tetrahydronaphthalen-2-ol, useful chiral catalysts in o
Synthesis of tetrahydronaphthyl thioureas as potent appetite suppressants
Bhandari, Kalpana,Srivastava, Shipra,Shankar, Girija
, p. 4189 - 4196 (2007/10/03)
A series of thiourea derivatives (7-23, 25-27) of 1- aminotetrahydronaphthalene (4) and 1-amino-2-hydroxytetrahydronaphthalene (5) were synthesized in single pot in 48-90% yield and evaluated for their anorexigenic activity. Among them compounds 10, 14, 15, 16 and 22 exhibited significant anorexigenic activity without any antidepressant effect and provided a new structural lead for appetite suppressants.
Synthesis of 1-amino-1,2,3,4-tetrahydronaphthalen-2-ols via epoxide ring opening as possible antidepressant and anorexigenic agents
Bhandari,Sharma,Singh,Shankar,Singh
, p. 468 - 471 (2007/10/03)
Thirteen 1-amino - 1,2,3,4 - tetrahydronaphthalen-2 - ols 5-17 have been synthesized via epoxide ring opening with various amines. The products are invariably trans with amine residue being attached regioselectively at position 1. The structures have been elucidated by elemental analyses and mass, IR and 1H NMR spectral data. These compounds have been tested for their effect on gross behaviour, antidepressant and anorexigenic activities. No effect is observed on gross behaviour whereas some compounds exhibit weak to moderate antidepressant (7, 12 and 17) and anorexigenic activity (7, 10, 11, 13, 15 and 16).
Catalytic asymmetric synthesis of secondary alcohols using chiral cis-amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene as chiral ligand
Bellucci, Cristina M.,Bergamini, Antonio,Cozzi, Pier Giorgio,Papa, Angelo,Tagliavini, Emilio,Umani-Ronchi, Achille
, p. 895 - 902 (2007/10/03)
The synthesis and resolution of cis-1-amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene 5 by a simple and straightforward methodology has been achieved. The homochiral aminoalcohol has been used in the catalytic reduction of ketones by means of BH3 · SMe2 affording secondary alcohols in high enantiomeric excesses. On the contrary low enantiomeric excesses have been obtained when (1S,2R)-N,N-dibutyl-1-amino-2-hydroxytetrahydronaphthalene 11 has been used to catalyze the enantioselective addition of Et2Zn to benzaldehyde.
cis-1-Amino-1,2,3,4-tetrahydro-2-naphthalenol: Resolution and application to the catalytic enantioselective reduction of ketones
Higashijima, Shinji,Itoh, Hiroki,Senda, Yasuhisa,Nakano, Shigeru
, p. 3107 - 3110 (2007/10/03)
cis-1-Amino-1,2,3,4-tetrahydro-2-naphthalenol was synthesized and resolved via its diastereomeric salts. Asymmetric reduction of prochiral ketones was examined using this amino alcohol at various temperatures.
Regio and stereocontrolled synthesis of aryl cis aminoalcohols from cis glycols
Lakshman, Mahesh K.,Zajc, Barbara
, p. 2529 - 2532 (2007/10/03)
Reaction of aryl substituted cis diols with α-acetoxyisobutyryl chloride results in the formation of trans vicinal chlorohydrin acetates where the halide is benzylic. Displacement of chloride with azide ion, deprotection of the ester and reduction of the azide furnishes the requisite cis aminoalcohols. This facile four-step procedure results in the exclusive replacement of a benzylic hydroxyl with an amino group, with a net retention of stereochemistry. This set of transformations is generally applicable to a wide variety of cis diols, and the overall yields are excellent.
Regioselective Ring Opening of Polycyclic Aromatic Hydrocarbon Epoxides by Polymer-Supported N3- Anion
Lakshman, Maheshkumar,Nadkarni, Durgesh V.,Lehr, Roland E.
, p. 4892 - 4897 (2007/10/02)
The benzylic ring opening of some polycyclic aromatic hydrocarbon (PAH) tetrahydro epoxides and one diol epoxide has been achieved by Amberlite supported N3- ion, in a regio- and stereoselective manner.The resulting azidohydrins have been conve
