A one-pot preparation of N-2-mercaptobenzoyl-amino amides

被引：5

作者：

Bande, Robert J. ^{[1
]}

Appella, Daniel H. ^{[1
]}

Trenkle, William C. ^{[1
]}

机构：

[1] NIDDK, NIH, Bethesda, MD 20892 USA

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 32期

关键词：

HBTU; Amide formation; Thioester; Topical microbicide; HIV NUCLEOCAPSID PROTEIN; ACYL TRANSFER; INHIBITORS; INFECTIVITY; THIOESTERS; RESIDUES; AGENTS; NCP7;

D O I：

10.1016/j.tetlet.2011.05.115

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The HIV-1 nucleocapsid (NCp7), structurally defined by zinc-binding domains, participates in crucial stages of the HIV-1 lifecycle and is mutationally nonpermissive, making it an attractive anti-HIV target. Mode of action studies have shown that the secondary structure and activity of NCp7 can be disrupted by acyl transfer from N-2-mercaptobenzoyl-amino amides. We have developed an improved one-pot reaction that affords N-2-mercaptobenzoyl-amino acids on multi-gram scales. This synthetic route allows for rapid modular construction and has greatly expanded the scope of easily accessible potential NCp7 inhibitors. Published by Elsevier Ltd.

引用

收藏

页码：4103 / 4105

页数：3

相关论文

共 18 条

[1] A new class of anti-HIV-1 agents targeted toward the nucleocapsid protein NCp7: The 2,2'-dithiobisbenzamides [J].

Domagala, JM ;

Bader, JP ;

Gogliotti, RD ;

Sanchez, JP ;

Stier, MA ;

Song, YT ;

Prasad, JVNV ;

Tummino, PJ ;

Scholten, J ;

Harvey, P ;

Holler, T ;

Gracheck, S ;

Hupe, D ;

Rice, WG ;

Schultz, R .

BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (03) :569-579

[2] MAPPING OF FUNCTIONALLY IMPORTANT RESIDUES OF A CYSTEINE-HISTIDINE BOX IN THE HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 NUCLEOCAPSID PROTEIN [J].

DORFMAN, T ;

LUBAN, J ;

GOFF, SP ;

HASELTINE, WA ;

GOTTLINGER, HG .

JOURNAL OF VIROLOGY, 1993, 67 (10) :6159-6169

[3] Benzamide-based thiolcarbamates: A new class of HIV-1NCp7 inhibitors [J].

Goel, A ;

Mazur, SJ ;

Fattah, RJ ;

Hartman, TL ;

Turpin, JA ;

Huang, MJ ;

Rice, WG ;

Appella, E ;

Inman, JK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (05) :767-770

[4] BASIC-AMINO-ACIDS FLANKING THE ZINC FINGER OF MOLONEY MURINE LEUKEMIA-VIRUS NUCLEOCAPSID PROTEIN NCP10 ARE CRITICAL FOR VIRUS INFECTIVITY [J].

HOUSSET, V ;

DEROCQUIGNY, H ;

ROQUES, BP ;

DARLIX, JL .

JOURNAL OF VIROLOGY, 1993, 67 (05) :2537-2545

[5] Specificity of acyl transfer from 2-mercaptobenzamide thioesters to the HIV-1 nucleocapsid protein [J].

Jenkins, Lisa M. Miller ;

Hara, Toshiaki ;

Durell, Stewart R. ;

Hayashi, Ryo ;

Inman, John K. ;

Piquemal, Jean-Philip ;

Gresh, Nohad ;

Appella, Ettore .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :11067-11078

[6] Small-molecule inactivation of HIV-1 NCp7 by repetitive intracellular acyl transfer [J].

Jenkins, Lisa M. Miller ;

Ott, David E. ;

Hayashi, Ryo ;

Coren, Lori V. ;

Wang, Deyun ;

Xu, Qun ;

Schito, Marco L. ;

Inman, John K. ;

Appella, Daniel H. ;

Appella, Ettore .

NATURE CHEMICAL BIOLOGY, 2010, 6 (12) :887-889

[7] Efficient and practical syntheses of benzothiopyran derivatives [J].

Jung, JC ;

Kim, JC ;

Park, OS .

SYNTHETIC COMMUNICATIONS, 2000, 30 (07) :1193-1203

[8] A Copper-Catalyzed, pH-Neutral Construction of High-Enantiopurity Peptidyl Ketones from Peptidic S-Acylthiosalicylamides in Air at Room Temperature [J].

Liebeskind, Lanny S. ;

Yang, Hao ;

Li, Hao .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (08) :1417-1421

[9] Biophysical characterization of zinc ejection from HIV nucleocapsid protein by anti-HIV 2,2'-dithiobis[benzamides] and benzisothiazolones [J].

Loo, JA ;

Holler, TP ;

Sanchez, J ;

Gogliotti, R ;

Maloney, L ;

Reily, MD .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (21) :4313-4320

[10] Charged amino acid residues of human immunodeficiency virus type 1 nucleocapsid p7 protein involved in RNA packaging and infectivity [J].

Poon, DTK ;

Wu, J ;

Aldovini, A .

JOURNAL OF VIROLOGY, 1996, 70 (10) :6607-6616