74763-88-5Relevant academic research and scientific papers
Synthesis of alcohols from m-fluorophenylsulfones and dialkylboranes: Application to the C14-C35 building block of E7389
Liu, Lei,Henderson, James A.,Yamamoto, Akihiko,Bremond, Paul,Kishi, Yoshito
, p. 2262 - 2265 (2012/06/30)
The reaction of m-fluorophenylsulfone anions with dialkylboranes, followed by alkaline hydroperoxide oxidation, yields alcohols in high yields. Optimization of the process, scope and limitation, and application to the synthesis of one of the C14-C35 building blocks of E7389, a right half analogue of halichondrin B, are reported.
Catalytic asymmetric γ-alkylation of carbonyl compounds via stereoconvergent suzuki cross-couplings
Zultanski, Susan L.,Fu, Gregory C.
supporting information; experimental part, p. 15362 - 15364 (2011/11/11)
With the aid of a chiral nickel catalyst, enantioselective γ- (and I-) alkylations of carbonyl compounds can be achieved through the coupling of γ-haloamides with alkylboranes. In addition to primary alkyl nucleophiles, for the first time for an asymmetric cross-coupling of an unactivated alkyl electrophile, an arylmetal, a boronate ester, and a secondary (cyclopropyl) alkylmetal compound are shown to couple with significant enantioselectivity. A mechanistic study indicates that cleavage of the carbon-halogen bond of the electrophile is irreversible under the conditions for asymmetric carbon-carbon bond formation.
1-ORTHOFLUOROPHENYL SUBSTITUTED 1, 2 , 5-THIAZOLIDINEDIONE DERIVATIVES AS PTP-AS INHIBITORS
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Page/Page column 68, (2010/11/27)
Compounds of the formula (I) are inhibitors of protein tyrosine phosphatases (PTPases) and, thus, may be employed for the treatment of conditions mediated by PTPase activity. The compounds of the present invention may also be employed as inhibitors of other enzymes characterized with a phosphotyrosine binding region such as the SH2 domain. Accordingly, the compounds of formula (I) may be employed for prevention and/or treatment of insulin resistance associated with obesity, glucose intolerance, diabetes mellitus, hypertension and ischemic diseases of the large and small blood vessels, conditions that accompany type-2 diabetes, including hyperlipidemia, hypertriglyceridemia, atherosclerosis, vascular restenosis, irritable bowel syndrome, pancreatitis, adipose cell tumors and carcinomas such as liposarcoma, dyslipidemia, and other disorders where insulin resistance is indicated. In addition, the compounds of the present invention may be employed to treat and/or prevent cancer, osteoporosis, neurodegenerative and infectious diseases, and diseases involving inflammation and the immune system.
Expanding the substitution pattern of 2(1H)-pyrazinones via Suzuki and Heck reactions
Azzam, Rasha,De Borggraeve, Wim M.,Compernolle, Frans,Hoornaert, Georges J.
, p. 3953 - 3962 (2007/10/03)
Various 3,5-dichloropyrazinones were substituted at the C-3 position with (hetero)aryl, alkyl and alkenyl groups by means of Suzuki and Heck reactions. The methodology could be extended to reactions on the far less reactive C-5 position by transhalogenati
The enantioselective synthesis of α-amino acid derivatives via organoboranes
O'Donnell, Martin J.,Drew, Mark D.,Cooper, Jeremy T.,Delgado, Francisca,Zhou, Changyou
, p. 9348 - 9349 (2007/10/03)
Optically active (S)-α-amino acids are prepared in 54-95% ee (12 cases) by reaction of the Schiff base acetate of glycine tert-butyl ester with B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine, and base. The enantiomeric (R)-α-amino acids are available in 59-92% ee (3 cases) by using cinchonine as the chiral control element. Copyright
Solid-phase synthesis of unnatural α-amino acid derivatives using a resin-bound glycine cation equivalent
O'Donnell, Martin J.,Delgado, Francisca,Drew, Mark D.,Pottorf, Richard S.,Zhou, Changyou,Scott, William L.
, p. 5831 - 5835 (2007/10/03)
Unnatural amino acids were synthesized on solid-phase by reaction of a resin-bound Schiff base with organoboranes. This novel use of a resin-bound glycine cation equivalent allows for the preparation of a variety of amino acid structural types not readily available by the complementary anionic equivalent.
Second-generation peptidomimetic inhibitors of protein farnesyltransferase demonstrating improved cellular potency and significant in vivo efficacy
O'Connor, Stephen J.,Barr, Kenneth J.,Wang, Le,Sorensen, Bryan K.,Tasker, Andrew S.,Sham, Hing,Shi-Chung, Ng,Cohen, Jerome,Devine, Edward,Cherian, Sajeev,Saeed, Badr,Zhang, Haichao,Jang Yun, Lee,Warner, Robert,Tahir, Stephen,Kovar, Peter,Ewing, Patricia,Alder, Jeffrey,Mitten, Michael,Leal, Juan,Marsh, Kennan,Bauch, Joy,Hoffman, Daniel J.,Sebti, Said M.,Rosenberg, Saul H.
, p. 3701 - 3710 (2007/10/03)
The synthesis and evaluation of analogues of previously reported farnesyltransferase inhibitors, pyridyl benzyl ether 3 and pyridylbenzylamine 4, are described. Substitution of 3 at the 5-position of the core awl ring resulted in inhibitors of equator less potency against the enzyme and decreased efficacy in a cellular assay against Ras processing by the enzyme. Substitution of 4 at the benzyl nitrogen yielded 26, which showed improved efficacy and potency and yet presented a poor pharmacokinetic profile. Further modification afforded 30, which demonstrated a dramatically improved pharmacokinetic profile. Compounds 26 and 29 demonstrated significant in vivo efficacy in nude mice inoculated with MiaPaCa-2, a human pancreatic tumor- derived cell line.
