Methylenecyclopropane analogues of nucleosides:: Synthesis, absolute configuration, and enantioselectivity of antiviral effect of (R)-(-)- and (S)-(+)-synadenol

被引：3

作者：

Qiu, YL

Hempel, A

Camerman, N

Camerman, A

Geiser, F

Ptak, RG

Breitenbach, JM

Kira, T

Li, L

Gullen, E

Cheng, YC

Drach, JC

Zemlicka, J ^{[1
]}

机构：

[1] Wayne State Univ, Sch Med, Barbara Ann Karmanos Canc Inst, Detroit, MI 48201 USA

[2] Univ Toronto, Dept Biochem, Toronto, ON M5S 1A8, Canada

[3] Ardono Res, Seattle, WA 98105 USA

[4] Chiral Technol Inc, Exton, PA 19341 USA

[5] Yale Univ, Sch Med, Dept Pharmacol, New Haven, CT 06510 USA

[6] Univ Michigan, Sch Dent, Dept Biol & Mat Sci, Ann Arbor, MI 48019 USA

来源：

NUCLEOSIDES & NUCLEOTIDES | 1999年 / 18卷 / 4-5期

关键词：

D O I：

10.1080/15257779908041507

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Synthesis, absolute configuration and antiviral activity of enantiomeric antiviral agents (R)-(-)- and (S)-(+)-synadenol (2 and 3a) are described.

引用

页码：597 / 598

页数：2

共 50 条

[21] Resolution of racemic mixtures of carbocyclic analogues of nucleosides and assignment of their absolute configuration
Besada, P
Terán, C
Quezada, E
Seco, JM
Uriarte, E
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2001, 20 (4-7): : 1359 - 1361
[22] (R)-(-)-ADENALLENE AND (S)-(+)-ADENALLENE - SYNTHESIS, ABSOLUTE-CONFIGURATION, ENANTIOSELECTIVITY OF ANTIRETROVIRAL EFFECT, AND ENZYMATIC DEAMINATION (VOL 35, PG 4098, 1992)
MEGATI, S
GOREN, Z
SILVERTON, JV
ORLINA, J
NISHIMURA, H
SHIRASAKI, T
MITSUYA, H
ZEMLICKA, J
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (05) : 634 - 634
[23] Synthesis of (Z)-(2,3-bis-hydroxymethyl)methylenecyclopropane analogues of purine nucleosides
Chen, XC
Matstuni, S
Mitsuya, H
Zemlicka, J
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (03): : 265 - 274
[24] (Z)- and (E)-2-(1,2-Dihydroxyethyl)methylenecyclopropane Analogues of 2′-Deoxyadenosine and 2′-Deoxyguanosine. Synthesis of All Stereoisomers, Absolute Configuration, and Antiviral Activity
Zhou, Shaoman
Drach, John C.
Prichard, Mark N.
Zemlicka, Jiri
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (10) : 3397 - 3407
[25] (Z)- and (E)-[2-fluoro-2-(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines, a new class of methylenecyclopropane analogues of nucleosides:: Synthesis and antiviral activity
Zhou, SM
Kern, ER
Gullen, E
Cheng, YC
Drach, JC
Matsumi, S
Mitsuya, H
Zemlicka, J
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (27) : 6964 - 6972
[26] Enantioselective synthesis and absolute configuration of (R)-(+)-lunacridine and (S)-(+)-lunacrine
Anand, RC
Selvapalam, N
JOURNAL OF CHEMICAL RESEARCH-S, 1998, (01): : 6 - 7
[27] SYNTHESIS, ABSOLUTE-CONFIGURATION, AND ENANTIOSELECTIVITY OF ANTIRETROVIRAL EFFECT OF (R)-(-)-CYTALLENE AND (S)-(+)-CYTALLENE - LIPASE-CATALYZED ENANTIOSELECTIVE ACYLATIONS OF (+/-)-N-4-ACYLCYTALLENES
JONES, BCNM
SILVERTON, JV
SIMONS, C
MEGATI, S
NISHIMURA, H
MAEDA, Y
MITSUYA, H
ZEMLICKA, J
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (08) : 1397 - 1405
[28] Synthesis and antiviral activity of (Z)- and (E)-2,2-[bis(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines:: Second-generation methylenecyclopropane analogues of nucleosides
Zhou, SM
Breitenbach, JM
Borysko, KZ
Drach, JC
Kern, ER
Gullen, E
Cheng, YC
Zemlicka, J
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (03) : 566 - 575
[29] Synthesis of Cyclic and Acyclic Pyrimidine Nucleosides Analogues with Anticipated Antiviral Activity
El-Shehry, Mohamed F.
El Telbani, Emad M.
Hegab, Mohamed I.
ACTA CHIMICA SLOVENICA, 2018, 65 (02) : 401 - 406
[30] Methylene-gem-difluorocyclopropane analogues of nucleosides:: Synthesis, cyclopropene-methylenecyclopropane rearrangement, and biological activity
Wang, RF
Ksebati, MB
Corbett, TH
Kern, ER
Drach, JC
Zemlicka, J
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (23) : 4019 - 4022

← 1 2 3 4 5 →