(2R,3R,4S,5R)-2-[6-[[4-(hydroxyamino)phenyl]methylsulfanyl]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol | 143330-49-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (2R,3R,4S,5R)-2-[6-[[4-(hydroxyamino)phenyl]methylsulfanyl]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 143330-49-8
• 化学式: C₁₇H₁₉N₅O₅S
• 分子量: 405.434
• InChiKey: IRHLEBKURJWMKI-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  171
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  甲醇 、 S-(4-硝基苄基)-6-硫肌苷 、 丙烷-1-硫醇 反应 5.0h， 生成 对硝基苯乙醇 、 p-Nitrobenzylthiopropane 、 6-疏基嘌呤核苷 、 6-(propylthio)-9-(β-D-ribofuranosyl)purine 、 (2R,3R,4S,5R)-2-[6-[[4-(hydroxyamino)phenyl]methylsulfanyl]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol 、 6-<<4-benzyl>thio>-9-(β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Photochemistry of nucleoside transport inhibitor 6-S-benzylated thiopurine ribonucleosides. Implications for a new class of photoaffinity labels

  摘要：

  Photochemistry of the nucleoside transport inhibitor 6-[(4-nitrobenzyl)thio]-9-(beta-D-ribofuranosyl)purine (NBMPR, 1) yielded products from the initial homolytic cleavage of the benzyl-sulfur bond. Photoreduction of the nitro group also occurred to a minor extent. The quantum yield for the disappearance of 1 was approximately 0.04. Several photoproducts and secondary photoproducts were identified and confirmed by synthesis. Irradiation of 6-(benzylthio)-9-(beta-D-ribofuranosyl)purine (BMPR, 3) also resulted in the formation of products from benzyl-sulfur cleavage with a quantum yield of approximately 0.01.

  DOI：

  10.1021/jo00048a034

文献信息

• [EN] OTIC FORMULATIONS FOR DRUG-INDUCED OTOTOXICITY<br/>[FR] FORMULATIONS OTIQUES POUR L'OTOTOXICITÉ INDUITE PAR UN MÉDICAMENT
  申请人：OTONOMY INC

  公开号：WO2021087408A1

  公开（公告）日：2021-05-06

  Provided herein are methods for preventing and/or reducing the severity of drug induced ototoxicity. Provided herein are methods for recovery from hearing loss due to drug-induced ototoxicity.
• Photochemistry of nucleoside transport inhibitor 6-S-benzylated thiopurine ribonucleosides. Implications for a new class of photoaffinity labels
  作者：Steven A. Fleming、David B. Rawlins、Vicente Samano、Morris J. Robins

  DOI：10.1021/jo00048a034

  日期：1992.10

  Photochemistry of the nucleoside transport inhibitor 6-[(4-nitrobenzyl)thio]-9-(beta-D-ribofuranosyl)purine (NBMPR, 1) yielded products from the initial homolytic cleavage of the benzyl-sulfur bond. Photoreduction of the nitro group also occurred to a minor extent. The quantum yield for the disappearance of 1 was approximately 0.04. Several photoproducts and secondary photoproducts were identified and confirmed by synthesis. Irradiation of 6-(benzylthio)-9-(beta-D-ribofuranosyl)purine (BMPR, 3) also resulted in the formation of products from benzyl-sulfur cleavage with a quantum yield of approximately 0.01.