(1S,2S,3R,5R)-3-[2-(2-Amino-6-chloro-pyrimidin-4-ylamino)-6-chloro-pyrimidin-4-ylamino]-5-hydroxymethyl-cyclopentane-1,2-diol | 110223-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (1S,2S,3R,5R)-3-[2-(2-Amino-6-chloro-pyrimidin-4-ylamino)-6-chloro-pyrimidin-4-ylamino]-5-hydroxymethyl-cyclopentane-1,2-diol
• 英文别名: (1S,2S,3R,5R)-3-[[2-[(2-amino-6-chloropyrimidin-4-yl)amino]-6-chloropyrimidin-4-yl]amino]-5-(hydroxymethyl)cyclopentane-1,2-diol
• CAS: 110223-89-7
• 化学式: C₁₄H₁₇Cl₂N₇O₃
• 分子量: 402.24
• InChiKey: RQTGVJRDMCPZAF-OTGTWEQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  162.33
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  (+/-)-4α-amino-2α,3β-dihydroxy-1α-cyclopentanemethanol 、 2-氨基-4,6-二氯嘧啶 生成 (1S,2S,3R,5R)-3-[2-(2-Amino-6-chloro-pyrimidin-4-ylamino)-6-chloro-pyrimidin-4-ylamino]-5-hydroxymethyl-cyclopentane-1,2-diol
  参考文献：
  名称：

  VINCE, ROBERT;TURAKHIA, RAJESH H.;SHANNON, WILLIAM M.;ARNETT, GUSSIE, J. MED. CHEM., 30,(1987) N 11, 2026-2030

  摘要：

  DOI：

文献信息

• Synthesis and antiviral activity of carbocyclic analogs of xylofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines
  作者：Robert Vince、Rajesh H. Turakhia、William M. Shannon、Gussie Arnett

  DOI：10.1021/jm00394a017

  日期：1987.11

  (+/-)-(1 alpha,2 beta,3 alpha,5 alpha)-3-[(2,5-Diamino-6-chloro-4- pyrimidinyl)amino]-5-(hydroxymethyl)-1,2-cyclopentanediol (7) was synthesized from 2-amino-4,6-dichloropyrimidine and the carbocyclic xylofuranosylamine (+/-)-(1 alpha,2 beta,3 alpha,5 alpha)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol (2) by subsequent preparation of the 5-[(4-chlorophenyl)azo] derivative of the resulting pyrimidine and reduction of the azo moiety with zinc and acetic acid. The carbocyclic analogue of 2-amino-4-chloropurine xylofuranoside (8) and the corresponding 8-azapurine 11 were prepared from 7. The carbocyclic analogues xylofuranosylguanine (9), xylofuranosyl-2,6-diaminopurine (10), xylofuranosyl-8-azaguanine (13), and xylofuranosyl-8-aza-2,6-diaminopurine (14) were prepared from 8 and 11. Compounds 9 and 13 were active against herpes simplex virus (types 1 and 2), with 9 being the more potent against both viruses. Analogue 9 also exhibited potent activity against human cytomegalovirus and varicella-zoster virus.

  (+/-)-(1α,2β,3α,5α)-3-[(2,5-二氨基-6-氯-4-嘧啶基)氨基]-5-(羟甲基)-1,2-环戊二醇 (7) 是通过2-氨基-4,6-二氯嘧啶和由碳骨架组成的木糖呋喃核糖胺 (+/-)-(1α,2β,3α,5α)-3-氨基-5-(羟甲基)-1,2-环戊二醇 (2) 合成的。具体方法是先制备嘧啶的5-[(4-氯苯基)偶氮]衍生物，然后用锌和乙酸还原偶氮部分。化合物7用于制备2-氨基-4-氯嘌呤木糖呋喃核糖苷 (8) 的碳骨架类似物以及对应的8-偶氮嘌呤 (11)。由8和11进一步合成了木糖呋喃核糖苷鸟嘌呤 (9)、木糖呋喃核糖苷-2,6-二氨基嘌呤 (10)、木糖呋喃核糖苷-8-偶氮鸟嘌呤 (13) 和木糖呋喃核糖苷-8-偶氮-2,6-二氨基嘌呤 (14)。化合物9和13对单纯疱疹病毒 (1型和2型) 活性显著，其中9对两种病毒的活性更强。化合物9还对人类巨细胞病毒和水痘-带状疱疹病毒表现出显著活性。