L-758340

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: L-758340
• 英文别名: 9-{[1(R)-hydroxymethyl-2(S)-cyclohexyl]methyl}guanine；2-amino-9-[[(1S,2R)-2-(hydroxymethyl)cyclohexyl]methyl]-1H-purin-6-one
• 化学式: C₁₃H₁₉N₅O₂
• 分子量: 277.326
• InChiKey: NNUZPTLISFKQLP-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 phosphate buffer 、 porcine pancreatic lipase 、 四溴化碳 、 氢气 、 sodium hydride 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 141.0h， 生成 L-758340
  参考文献：
  名称：

  Resolution and stereoselective synthesis of the herpes thymidine kinase inhibitor L-653180

  摘要：

  Resolution of L-653180, (+/-)-9-{[(Z)-2-(hydroxymethyl)cyclohexyl]-methyl}guanine, a racemic, nonsubstrate inhibitor of HSV-TK, was achieved and the absolute stereochemistry of the enantiomers was determined. Enzyme inhibition was shown to reside in the enantiomer with [1S,2R] stereochemistry in the cyclohexyl sidechain. An enantioselective synthesis of the more active L-653180 stereoisomer was devised. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00019-0

文献信息

• Prodrugs of herpes TK inhibitors
  申请人：Merck & Co. Inc.

  公开号：US05663175A1

  公开（公告）日：1997-09-02

  Certain prodrugs such as ##STR1## are useful in the inhibition of herpes virus thymidine kinase, the prevention or treatment of recurrent infection by herpes virus, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of preventing or treating recurrent infection by herpes virus are also described.

  某些前药，如##STR1##，在抑制疱疹病毒胸苷激酶、预防或治疗疱疹病毒复发感染方面具有用处，无论是作为化合物、药用盐、药用成分，还是与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。还描述了预防或治疗疱疹病毒复发感染的方法。
• Resolution and stereoselective synthesis of the herpes thymidine kinase inhibitor L-653180
  作者：Derek J. Von Langen、R.L. Tolman

  DOI：10.1016/s0957-4166(97)00019-0

  日期：1997.3

  Resolution of L-653180, (+/-)-9-[(Z)-2-(hydroxymethyl)cyclohexyl]-methyl}guanine, a racemic, nonsubstrate inhibitor of HSV-TK, was achieved and the absolute stereochemistry of the enantiomers was determined. Enzyme inhibition was shown to reside in the enantiomer with [1S,2R] stereochemistry in the cyclohexyl sidechain. An enantioselective synthesis of the more active L-653180 stereoisomer was devised. (C) 1997 Elsevier Science Ltd.