Synthesis of pyrrolo[2,3-d]pyrimidines with 3-amino-2-hydroxypropyl substituents

被引：3

作者：

Muzychka, L. V. ^{[1
]}

Verves, E. V. ^{[1
]}

Yaremchuk, I. O. ^{[1
]}

Smolii, O. B. ^{[1
]}

机构：

[1] Natl Acad Sci Ukraine, Inst Bioorgan & Petr Chem, UA-02660 Kiev, Ukraine

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2012年 / 48卷 / 03期

关键词：

pyrimido[5 ',4 ':4,5]pyrrolo[2,1-c][1,4]oxazines; pyrrolo[2,3-d]pyrimidines; bromolactonization; CYTOSOLIC PHOSPHOLIPASE A(2)ALPHA; ANTIVIRAL ACTIVITY; POTENTIAL ANTIMETABOLITES; NONNUCLEOSIDE ANALOGS; NUCLEOSIDE ANALOGS; ACYCLIC ANALOGS; CYCLOMARIN-A; SANGIVAMYCIN; TOYOCAMYCIN; TUBERCIDIN;

D O I：

10.1007/s10593-012-1019-x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel route has been found for the synthesis of pyrimido[5',4':4,5]pyrrolo[2,1-c][1,4]oxazines. They are promising reagents for the preparation of pyrrolo[2,3-d]pyrimidine-6-carboxylic acid amides which contain a 3-amino-2-hydroxypropyl substituent in position 7 of the heterocyclic ring.

引用

页码：481 / 487

页数：7

共 31 条

[1] Synthesis and antiviral activity of 7-deazaneplanocin A against orthopoxviruses (vaccinia and cowpox virus) [J].

Arumugham, B ;

Kim, HJ ;

Prichard, MN ;

Kern, ER ;

Chu, CK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (02) :285-287

[2] SYNTHESIS AND ANTIVIRAL ACTIVITY OF SOME ACYCLIC AND C-ACYCLIC PYRROLO[2,3-D]PYRIMIDINE NUCLEOSIDE ANALOGS [J].

BENNETT, SM ;

NGUYENBA, N ;

OGILVIE, KK .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (08) :2162-2173

[3] The synthesis of vicinal amino alcohols [J].

Bergmeier, SC .

TETRAHEDRON, 2000, 56 (17) :2561-2576

[4] SYNTHESIS AND ANTI-DNA VIRAL ACTIVITIES IN-VITRO OF CERTAIN 2,4-DISUBSTITUTED-7-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE NUCLEOSIDES [J].

BHATTACHARYA, BK ;

OJWANG, JO ;

RANDO, RF ;

HUFFMAN, JH ;

REVANKAR, GR .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (20) :3957-3966

[5] Microwave-assisted epoxidation of simple alkenes in the presence of hydrogen peroxide [J].

Bogdal, D ;

Lukasiewicz, M ;

Pielichowski, J ;

Bednarz, S .

SYNTHETIC COMMUNICATIONS, 2005, 35 (23) :2973-2983

[6] Design, synthesis and QSAR studies on N-aryl heteroarylisopropanolamines, a new class of non-peptidic HIV-1 protease inhibitors [J].

Di Santo, R ;

Costi, R ;

Artico, M ;

Massa, S ;

Ragno, R ;

Marshall, GR ;

La Colla, P .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) :2511-2526

[7] 1-(5-Carboxyindol-1-yl)propan-2-one Inhibitors of Human Cytosolic Phospholipase A2α with Reduced Lipophilicity: Synthesis, Biological Activity, Metabolic Stability, Solubility, Bioavailability, And Topical in Vivo Activity [J].

Drews, Andreas ;

Bovens, Stefanie ;

Roebrock, Kirsten ;

Sunderkoetter, Cord ;

Reinhardt, Dirk ;

Schaefers, Michael ;

van der Velde, Andrea ;

Elfringhoff, Alwine Schulze ;

Fabian, Joerg ;

Lehr, Matthias .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (14) :5165-5178

[8] A NEW EFFICIENT ROUTE TO 5-SUBSTITUTED BETA-2'-DEOXYRIBOSYLPYRROLO[2,3-D]PYRIMIDINES - PALLADIUM-CATALYZED FUNCTIONALIZATIONS OF A C-5 TRIFLATE INTERMEDIATE [J].

EDSTROM, ED ;

WEI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :6902-6903

[9] Structure-activity relationship of heterobase-modified 2′-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication [J].

Eldrup, AB ;

Prhavc, M ;

Brooks, J ;

Bhat, B ;

Prakash, TP ;

Song, QL ;

Bera, S ;

Bhat, N ;

Dande, P ;

Cook, PD ;

Bennett, CF ;

Carroll, SS ;

Ball, RG ;

Bosserman, M ;

Burlein, C ;

Colwell, LF ;

Fay, JF ;

Flores, OA ;

Getty, K ;

LaFemina, RL ;

Leone, J ;

MacCoss, M ;

McMasters, DR ;

Tomassini, JE ;

Von Langen, D ;

Wolanski, B ;

Olsen, DB .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (21) :5284-5297

[10] SYNTHESIS, CYTO-TOXICITY, AND ANTIVIRAL ACTIVITY OF CERTAIN 7-[(2-HYDROXYETHOXY)METHYL]PYRROLO[2,3-D]PYRIMIDINE NUCLEOSIDES RELATED TO TOYOCAMYCIN AND SANGIVAMYCIN [J].

GUPTA, PK ;

NASSIRI, MR ;

COLEMAN, LA ;

WOTRING, LL ;

DRACH, JC ;

TOWNSEND, LB .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1420-1425

← 1 2 3 4 →