Organic Carbamates in Drug Design and Medicinal Chemistry

被引：566

作者：

Ghosh, Arun K. ^{[1
]}

Brindisi, Margherita

机构：

[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2015年 / 58卷 / 07期

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

页码：2895 / 2940

页数：46

共 340 条

[1] Nickel-catalyzed dehydrative transformation of CO2 to urethanes [J].

Abla, M ;

Choi, JC ;

Sakakura, T .

GREEN CHEMISTRY, 2004, 6 (10) :524-525

[2] Halogen-free process for the conversion of carbon dioxide to urethanes by homogeneous catalysis [J].

Abla, M ;

Choi, JC ;

Sakakura, T .

CHEMICAL COMMUNICATIONS, 2001, (21) :2238-2239

[3] Synthesis and kinetic studies of diphenyl 1-(N-peptidylamino)alkanephosphonate esters and their biotinylated derivatives as inhibitors of serine proteases and probes for lymphocyte granzymes [J].

Abuelyaman, AS ;

Jackson, DS ;

Hudig, D ;

Woodard, SL ;

Powers, JC .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1997, 344 (02) :271-280

[4] Ledipasvir and Sofosbuvir for Untreated HCV Genotype 1 Infection [J].

Afdhal, Nezam ;

Zeuzem, Stefan ;

Kwo, Paul ;

Chojkier, Mario ;

Gitlin, Norman ;

Puoti, Massimo ;

Romero-Gomez, Manuel ;

Zarski, Jean-Pierre ;

Agarwal, Kosh ;

Buggisch, Peter ;

Foster, Graham R. ;

Braeu, Norbert ;

Buti, Maria ;

Jacobson, Ira M. ;

Subramanian, G. Mani ;

Ding, Xiao ;

Mo, Hongmei ;

Yang, Jenny C. ;

Pang, Phillip S. ;

Symonds, William T. ;

McHutchison, John G. ;

Muir, Andrew J. ;

Mangia, Alessandra ;

Marcellin, Patrick .

NEW ENGLAND JOURNAL OF MEDICINE, 2014, 370 (20) :1889-1898

[5] Mechanism of carbamate inactivation of FAAH: Implications for the design of covalent inhibitors and in vivo functional probes for enzymes [J].

Alexander, JP ;

Cravatt, BF .

CHEMISTRY & BIOLOGY, 2005, 12 (11) :1179-1187

[6] DNA INTERSTRAND CROSS-LINKING BY 2,5-BIS(1-AZIRIDINYL)-1,6-BENZOQUINONE - NUCLEOTIDE-SEQUENCE PREFERENCES AND COVALENT STRUCTURE OF THE DG-TO-DG CROSS-LINKS AT 5'-D(GN(N)C) IN SYNTHETIC OLIGONUCLEOTIDE DUPLEXES [J].

ALLEY, SC ;

BRAMELD, KA ;

HOPKINS, PB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :2734-2741

[7] A novel bis-tetrahydrofuranylurethane-containing nonpeptidic protease inhibitor (PI), GRL-98065, is potent against multiple-PI-resistant human immunodeficiency virus in vitro [J].

Amano, Masayuki ;

Koh, Yasuhiro ;

Das, Debananda ;

Li, Jianfeng ;

Leschenko, Sofiya ;

Wang, Yuan-Fang ;

Boross, Peter I. ;

Weber, Irene T. ;

Ghosh, Arun K. ;

Mitsuya, Hiroaki .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2007, 51 (06) :2143-2155

[8]

[Anonymous], 1997, Bioorg Med Chem, V5, P461

[9] Hepatitis C virus NS3-4A serine protease inhibitors:: SAR of P′2 moiety with improved potency [J].

Arasappan, A ;

Njoroge, FG ;

Chan, TY ;

Bennett, F ;

Bogen, SL ;

Chen, K ;

Gu, H ;

Hong, L ;

Jao, E ;

Liu, YT ;

Lovey, RG ;

Parekh, T ;

Pike, RE ;

Pinto, P ;

Santhanam, B ;

Venkatraman, S ;

Vaccaro, H ;

Wang, H ;

Yang, X ;

Zhu, Z ;

Mckittrick, B ;

Saksena, AK ;

Girijavallabhan, V ;

Pichardo, J ;

Butkiewicz, N ;

Ingram, R ;

Malcolm, B ;

Prongay, A ;

Yao, N ;

Marten, B ;

Madison, V ;

Kemp, S ;

Levy, O ;

Lim-Wilby, M ;

Tamura, S ;

Gangulya, AK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (19) :4180-4184

[10] Recent advances in indium-promoted organic reactions [J].

Auge, Jacques ;

Lubin-Germain, Nadege ;

Uziel, Jacques .

SYNTHESIS-STUTTGART, 2007, (12) :1739-1764

← 1 2 3 4 5 6 7 8 9 10 →