(S)-((2R,3S,5R)-(3-hydroxy-5-(2-oxo-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-3(2H)-yl)-tetrahydrofuran-2-yl))methyl 2-amino-3-methylbutanoate hydrochloride | 956483-03-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-((2R,3S,5R)-(3-hydroxy-5-(2-oxo-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-3(2H)-yl)-tetrahydrofuran-2-yl))methyl 2-amino-3-methylbutanoate hydrochloride
• 英文别名: Fv-100；[(2R,3S,5R)-3-hydroxy-5-[2-oxo-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-3-yl]oxolan-2-yl]methyl (2S)-2-amino-3-methylbutanoate;hydrochloride
• CAS: 956483-03-7
• 化学式: C₂₇H₃₅N₃O₆*ClH
• 分子量: 534.052
• InChiKey: CAHTYTZOAVUCIU-ZMQZINMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  7

制备方法与用途

FV-100（瓦尼韦啶，CF-1743）是一种强效且选择性的双环核苷类似物，能够抑制水痘带状疱疹病毒（VZV），体外实验中的半数有效浓度低于纳摩尔级别。

反应信息

• 作为产物：
  描述：

  3-(2-脱氧-beta-D-赤式-呋喃戊糖基)-6-(4-戊基苯基)呋喃并[2,3-d]嘧啶-2(3H)-酮 5'-L-缬氨酸酯 以Quant.的产率得到(S)-((2R,3S,5R)-(3-hydroxy-5-(2-oxo-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-3(2H)-yl)-tetrahydrofuran-2-yl))methyl 2-amino-3-methylbutanoate hydrochloride
  参考文献：
  名称：

  ANTI-VIRAL PYRIMIDINE NUCLEOSIDE DERIVATIVES

  摘要：

  一种用于治疗或预防病毒感染的化合物，例如由水痘-带状疱疹病毒引起的水痘或带状疱疹，所述化合物具有通式（II）：其中X为O、S、NH或CH2，Y为O、S或NH，Z为O、S或CH2，R1为C1-6烷基，优选为正烷基，如正戊基或正己基，且R2和R3中的一个为OH，另一个为中性、非极性氨基酸基团，或其药学上可接受的盐或水合物。所述中性、非极性氨基酸基团R2或R3可以是（IV）：其中R4、R5、R6和R7各自独立地为H或C1-2烷基。在优选实施例中，R2或R3中的一个为缬氨酸、亮氨酸、异亮氨酸或丙氨酸，特别是缬氨酸。

  公开号：

  US20150072948A1

文献信息

• Anti-viral pyrimidine nucleoside analogues
  申请人：——

  公开号：US20030148967A1

  公开（公告）日：2003-08-07

  A compound having the formula (I) wherein Ar is an, optionally substituted, aromatic ring system, the aromatic ring system comprising one six-membered aromatic ring or two fused six-membered aromatic rings; R 8 and R 9 are each independently selected form the group comprising hydrogen, alkyl, cycloalkyl, halogens, amino, alkylamino, dialkylamino, nitro, cyano, alkyoxy, aryloxy, thiol, alkylthiol, arythiol, aryl; Q is selected from the group comprising O, S and CY 2 , where Y may be the same or different and is selected from H, alkyl and halogens; X is selected from the group comprising O, NH, S, N-alkyl, (CH 2 ) m where m is 1 to 10, and CY 2 where Y may be the same or different and is selected from hydrogen, alkyl and halogens; Z is selected from the group comprising O, S, NH, and N-alkyl; U″ is H and U′ is selected from H and CH 2 T, or U′ and U″ are joined so as to form a ring moiety including Q wherein U′—U″ together is respectively selected from the group comprising —CTH—CT′T″- and —CT=CT- and —CT′=CT′-, so as to provide ring moieties selected from the group comprising (a), (b) wherein: T is selected from the group comprising OH, H, halogens, O-alkyl, O-acyl, O-aryl, CN, NH 2 and N 3 ; T′ is selected from the group comprising H and halogens and, where more than one T′ is present, they may be the same or different; T″ is selected from the group comprising H and halogens; and W is selected from the group comprising H, a phosphate group and a pharmacologically acceptable salt, derivative or pro-drug thereof; with the proviso that when T is OAc and T′ and T″ are present and are H, Ar is not 4-(2-benzoxazolyl)phenyl. C 1 to C 10 alkyl and alkoxy substituents on the aromatic ring system of Ar are preferred. Compounds show anti-viral activity, for example with respect to varicella zoster virus.

  一种化合物的化学式为（I），其中Ar是一个可选择取代的芳香环系统，该芳香环系统包括一个六元芳香环或两个融合的六元芳香环；R8和R9各自独立地选自羟基，烷基，环烷基，卤素，氨基，烷基氨基，二烷基氨基，硝基，氰基，烷氧基，芳基氧基，硫醇，烷硫基，芳硫基，芳基；Q选自O，S和CY2的群，其中Y可以相同或不同，选自氢，烷基和卤素；X选自O，NH，S，N-烷基，（CH2）m，其中m为1到10，以及CY2，其中Y可以相同或不同，选自氢，烷基和卤素；Z选自O，S，NH和N-烷基；U″为H，U′选自H和CH2T，或U′和U″结合形成包括Q的环基，其中U′—U″分别选自—CTH—CT′T″-和—CT=CT-和—CT′=CT′-，从而提供选自（a），（b）的环基，其中：T选自OH，H，卤素，O-烷基，O-酰基，O-芳基，CN，NH2和N3；T′选自H和卤素，当存在多个T′时，它们可以相同或不同；T″选自H和卤素；W选自H，磷酸盐基团和药理学上可接受的盐，衍生物或前药；但是，当T为OAc且T′和T″存在且为H时，Ar不是4-（2-苯并噻唑基）苯基。偏好在Ar的芳香环系统上具有C1到C10的烷基和烷氧基取代基。该化合物表现出抗病毒活性，例如对带状疱疹病毒的活性。
• Method of Preparation of Antiviral Compounds and Useful Intermediates Thereof
  申请人：Wang Yanling

  公开号：US20130331561A1

  公开（公告）日：2013-12-12

  The invention is directed to processes for synthesizing bicyclic nucleoside antiviral compounds and for synthesizing the intermediates used in the process. The invention is also directed to novel intermediate compounds useful in the process. The anti-viral compounds are useful in the treatment of herpes zoster (i.e., varicella zoster virus, VZV, shingles) and for the prevention of post herpetic neuralgia (PHN) resulting from this viral infection.

  该发明涉及合成双环核苷类抗病毒化合物的过程以及用于该过程的中间体的合成。该发明还涉及在该过程中有用的新型中间体化合物。这些抗病毒化合物可用于治疗带状疱疹（即水痘-带状疱疹病毒，VZV，带状疱疹）并预防由该病毒感染引起的后遗神经痛（PHN）。
• [EN] METHOD OF PREPARATION OF ANTIVIRAL COMPOUNDS AND USEFUL INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS ANTIVIRAUX ET INTERMÉDIAIRES UTILES DE CEUX-CI
  申请人：INHIBITEX INC

  公开号：WO2012048202A3

  公开（公告）日：2012-07-26
• ANTI-VIRAL PYRIMIDINE NUCLEOSIDE DERIVATIVES
  申请人：UNIVERSITY COLLEGE CARDIFF CONSULTANTS LIMITED

  公开号：US20150072948A1

  公开（公告）日：2015-03-12

  A compound for use in the treatment or prophylaxis of viral infections such, for example as chicken pox or shingles caused by the Varicella Zoster virus, said compound having the general formula (II): wherein X is O, S, NH or CH 2 , Y is O, S or NH, Z is O, S or CH 2 , R 1 is C 1-6 alkyl, preferably n-alkyl, e.g., n-pentyl or n-hexyl, and one of R 2 and R 3 is OH, and the other of R 3 and R 2 is a neutral, non-polar amino acid moiety, or a pharmaceutically acceptable salt or hydrate thereof. Said neutral, non-polar amino acid moiety R 2 or R 3 may be (IV): in which R 4 , R 5 , R 6 and R 7 are each independently H or C 1-2 alkyl. In preferred embodiments, one of R 2 or R 3 is valine, leucine, isoleucine or alanine, particularly valine.

  一种用于治疗或预防病毒感染的化合物，例如由水痘-带状疱疹病毒引起的水痘或带状疱疹，所述化合物具有通式（II）：其中X为O、S、NH或CH2，Y为O、S或NH，Z为O、S或CH2，R1为C1-6烷基，优选为正烷基，如正戊基或正己基，且R2和R3中的一个为OH，另一个为中性、非极性氨基酸基团，或其药学上可接受的盐或水合物。所述中性、非极性氨基酸基团R2或R3可以是（IV）：其中R4、R5、R6和R7各自独立地为H或C1-2烷基。在优选实施例中，R2或R3中的一个为缬氨酸、亮氨酸、异亮氨酸或丙氨酸，特别是缬氨酸。