172324-67-3Relevant articles and documents
Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ-Lactams
Sietmann, Jan,Ong, Mike,Mück-Lichtenfeld, Christian,Daniliuc, Constantin G.,Wiest, Johannes M.
supporting information, p. 9719 - 9723 (2021/03/16)
Asymmetric access to γ-lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)-1-amino-2-indanol for chiral induction. Mechanistic analysis of the key N,O-ketal rearrangement reveals a Curtin–Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ-lactams, including those bearing all-carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further demonstrates the synthetic utility and highlights the general applicability of the presented method.
SUBSTITUTED SPIROPYRIDO[1,2-a]PYRAZINE DERIVATIVE AND PHARMACEUTICAL USE OF SAME AS HIV INTEGRASE INHIBITOR
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Paragraph 1421; 1422; 1423, (2014/08/19)
Provided is a substituted spiropyrido[1,2-a]pyrazine derivative or a pharmaceutically acceptable salt thereof, which is useful as an anti-HIV agent. The present invention relates to a compound represented by the following formula [I] or [II] or a pharmace
Direct syntheses of spiro- and fused-hydrofurans by a tunable tandem semipinacol rearrangement/oxa-michael addition protocol
Li, Bao-Sheng,Liu, Wen-Xing,Zhang, Qing-Wei,Wang, Shao-Hua,Zhang, Fu-Min,Zhang, Shu-Yu,Tu, Yong-Qiang,Cao, Xiao-Ping
supporting information, p. 5246 - 5249 (2013/05/22)
A highly chemoselective one-pot reaction has been developed involving a tandem semipinacol rearrangement/oxa-Michael addition sequence in which the in situ generated ketol diene intermediate can be transformed specifically to either the spiro- or fused-dihydrofuran products (see scheme). This one-pot tandem reaction represents a general synthetic methodology for the syntheses of the two different kinds of furan derivatives. Copyright
BORON COMPOUND WITH AMINO ACID SKELETON CONTAINING CYCLO RING
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Paragraph 0054; 0055, (2013/06/27)
The purpose of the present invention is to provide a novel boron-containing compound utilizable in BNCT and so on and a process for preparing same. According to the process, a boron compounds having an amino acid skeleton containing cyclo-type rings or a
Pre-steady state kinetic analysis of cyclobutyl derivatives of 2′-deoxyadenosine 5′-triphosphate as inhibitors of HIV-1 reverse transcriptase
Kim, Jiae,Wang, Ligong,Li, Yongfeng,Becnel, Kimberlynne D.,Frey, Kathleen M.,Garforth, Scott J.,Prasad, Vinayaka R.,Schinazi, Raymond F.,Liotta, Dennis C.,Anderson, Karen S.
supporting information; experimental part, p. 4064 - 4067 (2012/07/14)
Pre-steady state kinetic analysis was utilized for biochemical evaluation of a series of cyclobutyl adenosine nucleotide analogs with HIV-1 RT WT. The phosphonyl-diphosphate form of the cyclobutyl nucleotide, 5, was the most efficiently incorporated of the series. Nucleotide 5 was fourfold more efficiently incorporated than the FDA approved TFV-DP by RTWT. The kinetics of incorporation for 5 using the drug resistant mutant enzyme K65R was also determined. Compound 5 was threefold more efficiently incorporated compared to TFV-DP with RTK65R. These results demonstrate cyclobutyl adenosine analogs can act as substrates for incorporation by HIV-1 RT and be a potential scaffold for HIV inhibitors.
Discovery of two clinical histamine H3 receptor antagonists: Trans - N -ethyl-3-fluoro-3-[3-fluoro-4-(pyrrolidinylmethyl)phenyl] cyclobutanecarboxamide (PF-03654746) and trans -3-fluoro-3-[3-fluoro-4- (pyrrolidin-1-ylmethyl)phenyl]- N -(2-methy
Wager, Travis T.,Pettersen, Betty A.,Schmidt, Anne W.,Spracklin, Douglas K.,Mente, Scot,Butler, Todd W.,Howard, Harry,Lettiere, Daniel J.,Rubitski, David M.,Wong, Diane F.,Nedza, Frank M.,Nelson, Frederick R.,Rollema, Hans,Raggon, Jeffrey W.,Aubrecht, Jiri,Freeman, Jody K.,Marcek, John M.,Cianfrogna, Julie,Cook, Karen W.,James, Larry C.,Chatman, Linda A.,Iredale, Philip A.,Banker, Michael J.,Homiski, Michael L.,Munzner, Jennifer B.,Chandrasekaran, Rama Y.
, p. 7602 - 7620 (2012/01/05)
The discovery of two histamine H3 antagonist clinical candidates is disclosed. The pathway to identification of the two clinical candidates, 6 (PF-03654746) and 7 (PF-03654764) required five hypothesis driven design cycles. The key to success i
PYRAZOLOTHIAZOLE COMPOUND
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Page/Page column 23, (2011/04/25)
A compound represented by the formula (I) or pharmacologically acceptable salt thereof exhibits an excellent CRF receptor antagonism wherein X is a nitrogen atom or CH; R1 is -A11-A12; A11 is a single bond or a C1-6 alkylene group; A12 is a hydrogen atom, a C1-6 alkyl group or a C3-6 cycloalkyl group, etc.; R2 is -A21-A22; A21 is a single bond or a C1-6 alkylene group; A22 is a hydrogen atom, a C1-6 alkyl group, a C3-6 cycloalkyl group, a non-aromatic heterocyclic group, or a heteroaryl group, etc.; R3 is a C 1-6 alkyl group, a C3-6 cycloalkyl group, a C1-6 alkoxy group, a C3-6 cycloalkoxy C1-6 alkyl group, di-C1-6 alkyl amino group, a halogen atom, a cyano group, a formyl group, or a carboxyl group, etc; R4 is a hydrogen atom or a C1-6 alkoxy group; R5 is a halogen atom, a C1-6 alkyl group, or a C1-6 alkoxy group; R6 is a hydrogen atom, a C1-6 alkyl group, a C1-6 alkoxy group, a C1-6 alkylthio group, or a C1-6 alkyl sulfinyl group etc.; and R7 is a C1-6 alkyl group, a C1-6 alkoxy group, or a C1-6 alkylthio group
The discovery and structure-activity relationships leading to CE-156811, a difluorophenyl cyclopropyl fluoroether: A novel potent antibacterial analog derived from hygromycin A
Le, Phuong T.,Brickner, Steven J.,Wade, Sarah K.,Brighty, Katherine,Monahan, Rhonda,Stone, Gregory G.,Girard, Dennis,Finegan, Steve,Duignan, Joan,Schafer, John,Maloney, Meghan,Zaniewski, Richard P.,Connolly, Ann G.,Liras, Jennifer,Bordner, Jon,Samardjiev, Ivan
scheme or table, p. 276 - 279 (2011/02/27)
SAR studies and optimization of various modified Hygromycin A fluoroalkyl ethers, which led to the discovery of the highly potent 4′-(2-cyclopropyl- 2-fluoroethyl ether) antibacterial CE-156811 (1) derived from truncation of the ribose ring and difluorination of the phenyl found in Hygromycin A, are discussed.
D3 AND 5-HT2A RECEPTOR MODULATORS
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Page/Page column 74, (2010/04/23)
The present invention provides compounds of the general formula (I) wherein X, n and R1 are as described herein, as well as pharmaceutically acceptable salts and esters thereof, methods for their manufacture, pharmaceutical compositions contain
Palladium-catalyzed diastereo- and enantioselective Wagner-Meerwein shift: Control of absolute stereochemistry in the C-C bond migration event
Trost, Barry M.,Xie, Jia
, p. 6231 - 6242 (2008/12/20)
Inducing absolute stereochemistry in Wagner-Meerwein shifts was examined in a ring expansion protocol. Initiated by generation of a π-allylpalladium intermediate by hydropalladation of allenes, the ring expansion of allenylcyclobutanol substrates proceeded with excellent diastereo- and enantioselectivities. The results demonstrate that, during the C-C bond migration process, our chiral catalysts can control the stereochemistry of both the π-allylpalladium intermediate and the corresponding migration bond. Moreover, the stereochemical outcome of the reaction can be rationalized very well with the working model of the chiral catalyst. The method provides an efficient way to synthesize highly substituted cyclopentanones with an α-chiral O-tertiary center which has various synthetic applications.
