Organic Carbamates in Drug Design and Medicinal Chemistry

被引:580
作者
Ghosh, Arun K. [1 ]
Brindisi, Margherita
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
基金
美国国家卫生研究院;
关键词
HIV-1 PROTEASE INHIBITORS; GAMMA-SECRETASE INHIBITOR; ENZYME PRODRUG THERAPY; SOLID-PHASE SYNTHESIS; AMINOMETHYL)-1-CYCLOHEXANE ACETIC-ACID; TRIFLUOROMETHYL KETONE INHIBITORS; IMMUNODEFICIENCY-VIRUS PROTEASE; CYCLIZATION-ACTIVATED PRODRUGS; IMPROVED ORAL BIOAVAILABILITY; APPENDED N-ALKYLSULFONAMIDES;
D O I
10.1021/jm501371s
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The carbamate group is a key structural motif in many approved drugs and prodrugs. There is an increasing use of carbamates in medicinal chemistry and many derivatives are specifically designed to make drugtarget interactions through their carbamate moiety. In this Perspective, we present properties and stabilities of carbamates, reagents and chemical methodologies for the synthesis of carbamates, and recent applications of carbamates in drug design and medicinal chemistry.
引用
收藏
页码:2895 / 2940
页数:46
相关论文
共 340 条
[21]   NONPEPTIDIC INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE .6. DESIGN OF A POTENT, INTRATRACHEALLY ACTIVE, PYRIDONE-BASED TRIFLUOROMETHYL KETONE [J].
BERNSTEIN, PR ;
GOMES, BC ;
KOSMIDER, BJ ;
VACEK, EP ;
WILLIAMS, JC .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (01) :212-215
[22]  
Best BM, 2008, EXPERT OPIN DRUG MET, V4, P965, DOI [10.1517/17425255.4.7.965, 10.1517/17425255.4.7.965 ]
[23]   Quantitative measurement of changes in amyloid-β(40) in the rat brain and cerebrospinal fluid following treatment with the γ-secretase inhibitor LY-411575 [N2-[(2S)-2-(3,5-difluorophenyl)-2-hydroxyethanoyl]-N1-[(7S)-5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-L-alaninamide] [J].
Best, JD ;
Jay, MT ;
Otu, F ;
Ma, J ;
Nadin, A ;
Ellis, S ;
Lewis, HD ;
Pattison, C ;
Reilly, M ;
Harrison, T ;
Shearman, MS ;
Williamson, TL ;
Atack, JR .
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2005, 313 (02) :902-908
[24]   General approach to the coupling of organoindium reagents with imines via copper catalysis [J].
Black, DA ;
Arndtsen, BA .
ORGANIC LETTERS, 2006, 8 (10) :1991-1993
[25]  
Blakey DC, 1996, CANCER RES, V56, P3287
[26]   A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol [J].
Blankman, Jacqueline L. ;
Simon, Gabriel M. ;
Cravatt, Benjamin F. .
CHEMISTRY & BIOLOGY, 2007, 14 (12) :1347-1356
[27]   KF/Al2O3 mediated organic synthesis [J].
Blass, BE .
TETRAHEDRON, 2002, 58 (46) :9301-9320
[28]   Depeptidization efforts on P3-P′2 α-ketoamide inhibitors of HCVNS3-4A serine protease:: Effect on HCV replicon activity [J].
Bogen, SL ;
Ruan, S ;
Liu, R ;
Agrawal, S ;
Pichardo, J ;
Prongay, A ;
Baroudy, B ;
Saksena, AK ;
Girijavallabhan, V ;
Njoroge, FG .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (06) :1621-1627
[29]   Discovery of SCH446211 (SCH6): A new ketoamide inhibitor of the HCV NS3 serine protease and HCV subgenomic RNA replication [J].
Bogen, SL ;
Arasappan, A ;
Bennett, F ;
Chen, K ;
Jao, E ;
Liu, YT ;
Lovey, RG ;
Venkatraman, S ;
Pan, WD ;
Parekh, T ;
Pike, RE ;
Ruan, S ;
Liu, R ;
Baroudy, B ;
Agrawal, S ;
Chase, R ;
Ingravallo, P ;
Pichardo, J ;
Prongay, A ;
Brisson, JM ;
Hsieh, TY ;
Cheng, KC ;
Kemp, SJ ;
Levy, OE ;
Lim-Wilby, M ;
Tamura, SY ;
Saksena, AK ;
Girijavallabhan, V ;
Njoroge, FG .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (09) :2750-2757
[30]   New aza-dipeptide analogues as potent and orally absorbed HIV-1 protease inhibitors:: Candidates for clinical development [J].
Bold, G ;
Fässler, A ;
Capraro, HG ;
Cozens, R ;
Klimkait, T ;
Lazdins, J ;
Mestan, J ;
Poncioni, B ;
Rösel, J ;
Stover, D ;
Tintelnot-Blomley, M ;
Acemoglu, F ;
Beck, W ;
Boss, E ;
Eschbach, M ;
Hürlimann, T ;
Masso, E ;
Roussel, S ;
Ucci-Stoll, K ;
Wyss, D ;
Lang, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (18) :3387-3401