Regioselective synthesis of the novel N4-substituted pyrazolo[4,5-e][1,2,4]thiadiazines as potent HIV-1 NNRTIs

被引：3

作者：

Liu, Xinyong ^{[1
]}

Chen, Niangen

Yan, Renzhang

Xu, Wenfang

Molina, Maria Teresa

Vega, Salvador

机构：

[1] Shandong Univ, Sch Pharm, Inst Med Chem, Jinan 250012, Peoples R China

[2] CSIC, Inst Quim Med, E-28006 Madrid, Spain

来源：

HETEROCYCLES | 2006年 / 68卷 / 06期

关键词：

D O I：

10.3987/COM-06-10707

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new ring system of 7-methylpyrazolo[4,5-e][1,2,4]thiadiazine (5) was synthesized. Starting from 5 a series of novel mono N-4-substituted derivatives (6) were prepared regioselectively and evaluated as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs).

引用

页码：1225 / +

页数：9

共 12 条

[1] Novel 1,1,3-trioxo-2H,4H-thieno [3,4-e][1,2,4] thiadiazine derivatives as non-nucleoside reverse transcriptase inhibitors that inhibit human immunodeficiency virus type 1 replication [J].

Arranz, E ;

Díaz, JA ;

Ingate, ST ;

Witvrouw, M ;

Pannecouque, C ;

Balzarini, J ;

De Clercq, E ;

Vega, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (21) :4109-4117

[2]

Arranz ME, 1997, HETEROCYCLES, V45, P1767

[3] Synthesis and anti-HIV activity of 1,1,3-trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazines (TTDs):: A new family of HIV-1 specific non-nucleoside reverse transcriptase inhibitors [J].

Arranz, ME ;

Díaz, JA ;

Ingate, ST ;

Witvrouw, M ;

Pannecouque, C ;

Balzarini, J ;

De Clercq, E ;

Vega, S .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (12) :2811-2822

[4]

Bormann D., 1980, ANNU REP MED CHEM, V15, P100

[5]

BUCHHOLZ RA, 1993, ANNU REP MED CHEM, V28, P69

[6] Novel bronchodilators:: Synthesis, transamination reactions, and pharmacology of a series of pyrazino[2,3-c][1,2,6]thiadiazine 2,2-dioxides [J].

Campillo, N ;

García, C ;

Goya, P ;

Alkorta, I ;

Páez, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (22) :4219-4227

[7]

Holla BS, 2001, FARMACO, V56, P565

[8] Imidazothiadiazine dioxides:: Synthesis and antiviral activity [J].

Martínez, A ;

Esteban, AI ;

Herrero, A ;

Ochoa, C ;

Andrei, G ;

Snoeck, R ;

Balzarini, J ;

De Clercq, E .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (08) :1617-1623

[9] Bioisosterism: A rational approach in drug design [J].

Patani, GA ;

LaVoie, EJ .

CHEMICAL REVIEWS, 1996, 96 (08) :3147-3176

[10] 4H-1,2,4-pyridothiadiazine 1,1-dioxides and 2,3-dihydro-4H-1,2,4-pyridothiadiazine 1,1-dioxides chemically related to diazoxide and cyclothiazide as powerful positive allosteric modulators of (R/S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors:: Design, synthesis, pharmacology, and structure-activity relationships [J].

Pirotte, B ;

Podona, T ;

Diouf, O ;

de Tullio, P ;

Lebrun, P ;

Dupont, L ;

Somers, F ;

Delarge, J ;

Morain, P ;

Lestage, P ;

Lepagnol, J ;

Spedding, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (16) :2946-2959

← 1 2 →