STRUCTURE OF 1-(S)-(3-HYDROXY-2-PHOSPHONYLMETHOXYPROPYL)CYTOSINE - AN ANTIVIRAL AGENT

被引：1

作者：

SYMERSKY, J ^{[2
]}

HOLY, A

机构：

[1] CZECHOSLOVAK ACAD SCI, INST ORGAN CHEM & BIOCHEM, CS-16610 PRAGUE 6, CZECHOSLOVAKIA

[2] UNIV OKLAHOMA, DEPT CHEM & BIOCHEM, NORMAN, OK 73019 USA

[3] CZECHOSLOVAK ACAD SCI, INST ORGAN CHEM & BIOCHEM, CS-16610 PRAGUE 6, CZECHOSLOVAKIA

来源：

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY | 1991年 / 47卷

关键词：

D O I：

10.1107/S0108270190013257

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

4-Amino-1-(S)-{2-[(dihydroxyphosphoryl)-methoxy]-3-hydroxypropyl}-2(1H)-pyrimidinone, C8H14N3O6P, M(r) = 279.19, orthorhombic, P2(1)2(1)2(1), a = 6.926 (1), b = 9.084 (2), c = 18.602 (3) angstrom, V = 1170.4 (4) angstrom 3, Z = 4, D(x) = 1.58 (1) Mg m-3, lambda(Cu K-alpha) = 1.54178 angstrom, mu = 2.4 mm-1, F(000) = 584, T = 168 K, final R = 0.024 for 1393 unique observed reflections. The molecule has been found to exist in a folded zwitterionic form where the negatively charged phosphonyl group and the positively charged cytosine ring are in proximity. The crystal packing involves significant intermolecular hydrogen-bond contacts.

引用

页码：2104 / 2107

页数：4

共 50 条

[31] Antiviral activity of triazine analogues of 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine (cidofovir) and related compounds
Krecmerova, Marcela
Holy, Antonin
Piskala, Alois
Masojidkova, Milena
Andrei, Graciela
Naesens, Lieve
Neyts, Johan
Balzarini, Jan
De Clercq, Erik
Snoeck, Robert
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (05) : 1069 - 1077
[32] ACYCLIC NUCLEOTIDE ANALOGS .2. SYNTHESIS OF POTENTIAL PRODRUGS AND METABOLITES OF 9-(S)-(3-HYDROXY-2-PHOSPHONYLMETHOXYPROPYL)ADENINE
ROSENBERG, I
HOLY, A
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1987, 52 (11) : 2792 - 2800
[33] Treatment of severe laryngeal papillomatosis with intralesional injections of Cidofovir(R) [(S)-1-(3-Hydroxy-Phosphonylmethoxypropyl) Cytosine, HPMPC, Vistide(R)]
Wellens, W
Snoeck, R
Desloovere, C
VanRanst, M
Naesens, L
DeClercq, E
Feenstra, L
SYDNEY '97 - XVI WORLD CONGRESS OF OTORHINOLARYNGOLOGY HEAD AND NECK SURGERY, TOMES 1 AND 2, 1996, : 455 - 459
[34] The antiviral agent cidofovir [(S)-1-(3-hydroxy-2-phosphonyl-methoxypropyl)cytosine] has pronounced activity against nasopharyngeal carcinoma grown in nude mice
Neyts, J
Sadler, R
De Clercq, E
Raab-Traub, N
Pagano, JS
CANCER RESEARCH, 1998, 58 (03) : 384 - 388
[35] ISOLATION OF EQUINE HERPESVIRUS-1 MUTANTS IN THE PRESENCE OF (S)-9-(3-HYDROXY-2-PHOSPHONYLMETHOXYPROPYL)ADENINE - DEMONSTRATION OF RESISTANCE INVITRO AND INVIVO
FIELD, HJ
AWAN, AR
DELAFUENTE, R
ANTIVIRAL RESEARCH, 1991, 16 (01) : 29 - 39
[36] INHIBITION OF AFRICAN SWINE FEVER VIRUS-DNA SYNTHESIS BY (S)-9-(3-HYDROXY-2-PHOSPHONYLMETHOXYPROPYL)ADENINE
ARZUZA, O
GARCIAVILLALON, D
TABARES, E
GILFERNANDEZ, C
DECLERCQ, E
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1988, 154 (01) : 27 - 32
[37] A concise and simple synthesis of 1-hydroxy-phenethylamine derivatives: Formal synthesis of naturally occurring norephedrine, virolin and 3-hydroxy-2-phosphonylmethoxypropyl adenine
S SAHA
P CHAKRABORTY
S C ROY
Journal of Chemical Sciences, 2014, 126 : 837 - 846
[38] A concise and simple synthesis of 1-hydroxy-phenethylamine derivatives: Formal synthesis of naturally occurring norephedrine, virolin and 3-hydroxy-2-phosphonylmethoxypropyl adenine
Saha, S.
Chakraborty, P.
Roy, S. C.
JOURNAL OF CHEMICAL SCIENCES, 2014, 126 (03) : 837 - 846
[39] THE EFFECT OF (S)-9-(3-HYDROXY-2-PHOSPHONYLMETHOXYPROPYL) ADENINE ON NUCLEAR AND ORGANELLAR DNA-SYNTHESIS IN ERYTHROCYTIC SCHIZOGONY IN MALARIA
SMEIJSTERS, LJJW
ZIJLSTRA, NM
DEVRIES, E
FRANSSEN, FFJ
JANSE, CJ
OVERDULVE, JP
MOLECULAR AND BIOCHEMICAL PARASITOLOGY, 1994, 67 (01) : 115 - 124
[40] A NEW SYNTHESIS OF THE POTENT AND SELECTIVE ANTI-HERPESVIRUS AGENT (S)-1-[3-HYDROXY-2-(PHOSPHONYLMETHOXY)PROPYL]CYTOSINE
BRONSON, JJ
FERRARA, LM
HOWELL, HG
BRODFUEHRER, PR
MARTIN, JC
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1990, 9 (06): : 745 - 769

← 1 2 3 4 5 →