6-benzylsulfanyl-2-iodo-9-isopropyl-9H-purine | 403620-92-8

• 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: 6-benzylsulfanyl-2-iodo-9-isopropyl-9H-purine
• 英文别名: 6-benzylthio-2-iodo-9-isopropyl-9H-purine；9H-Purine, 2-iodo-9-(1-methylethyl)-6-[(phenylmethyl)thio]-；6-benzylsulfanyl-2-iodo-9-propan-2-ylpurine
• CAS: 403620-92-8
• 化学式: C₁₅H₁₅IN₄S
• 分子量: 410.281
• InChiKey: FQDJMJLHRAPUJW-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  550.6±60.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-benzylsulfanyl-2-iodo-9-isopropyl-9H-purine 在 tris(dibenzylideneacetone)dipalladium (0) 间氯过氧苯甲酸 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(9-isopropyl-6-phenylmethanesulfonyl-9H-purin-2-yl)-3-methyl-butyramide
  参考文献：
  名称：

  A Pd(0) based cross-coupling approach to the synthesis of 2-amidopurines and their evaluation as CDK inhibitors

  摘要：

  Two new series of 2-amido- and 2-aminocarbonylpurines have been synthesized using a Pd catalyst cross-coupling reaction either with amides or amines in the presence of CO. Moderate in vitro inhibitory activity against CDK1 and CDK5 was observed with IC50 of 0-9 mu M for the most active compound (18c). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.003
• 作为产物：
  描述：

  2-碘-6-氯嘌呤 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 生成 6-benzylsulfanyl-2-iodo-9-isopropyl-9H-purine
  参考文献：
  名称：

  Novel R-roscovitine NO-donor hybrid compounds as potential pro-resolution of inflammation agents

  摘要：

  Neutrophils play a pivotal role in the pathophysiology of multiple human inflammatory diseases. Novel pharmacological strategies which drive neutrophils to undergo programmed cell death (apoptosis) have been shown to facilitate the resolution of inflammation. Both the cyclin-dependent kinase inhibitor (CDKi) R-roscovitine and nitric oxide (NO) have been shown to enhance apoptosis of neutrophils and possess pro-resolution of inflammation properties. In order to search for new multi-target pro-resolution derivatives, here we describe the design, synthesis and investigation of the biological potential of a small series of hybrid compounds obtained by conjugating R-roscovitine with two different NO-donor moieties (compounds 2, 9a, 9c). The synthesized compounds were tested as potential pro-resolution agents, with their ability to promote human neutrophil apoptosis evaluated. Both compound 9a and 9c showed an increased pro-apoptotic activity when compared with either R-roscovitine or structurally related compounds devoid of the ability to release NO (des-NO analogues). Inhibition of either NO-synthase or soluble guanylate cyclase did not affect the induction of apoptosis by the R-roscovitine derivatives, similar to that reported for other classes of NO-donors. In contrast the NO scavenger PTIO prevented the enhanced apoptosis seen with compound 9a over R-roscovitine. These data show that novel compounds such as CDKi-NO-donor hybrids may have additive pro-resolution of inflammation effects. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.009

文献信息

• Cyclin-dependent kinase (CDK) inhibitors: development of a general strategy for the construction of 2,6,9-trisubstituted purine libraries. Part 1
  作者：Virginie Brun、Michel Legraverend、David S Grierson

  DOI：10.1016/s0040-4039(01)01751-8

  日期：2001.11

  To validate a proposed solid support synthesis strategy for the construction of 2,6,9-trisubstituted purine based CDK inhibitors, the N-9 THP protected 6-benzylthio-2-iodopurine 11 was reacted with piperidine-2-methanol to give 12. Alternatively, intermediate It was converted to the C-2 acetylenyl substituted purine 16 in five steps, involving N-9 alkylation (Mitsunobu reaction), a Pd(0)-CuI-catalyzed acetylene coupling, selective activation of the 6-sulfur substituent and its displacement by ArCH2NH2. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Novel R-roscovitine NO-donor hybrid compounds as potential pro-resolution of inflammation agents
  作者：Gabriele Montanaro、Massimo Bertinaria、Barbara Rolando、Roberta Fruttero、Christopher D. Lucas、David A. Dorward、Adriano G. Rossi、Ian L. Megson、Alberto Gasco

  DOI：10.1016/j.bmc.2013.01.009

  日期：2013.4

  Neutrophils play a pivotal role in the pathophysiology of multiple human inflammatory diseases. Novel pharmacological strategies which drive neutrophils to undergo programmed cell death (apoptosis) have been shown to facilitate the resolution of inflammation. Both the cyclin-dependent kinase inhibitor (CDKi) R-roscovitine and nitric oxide (NO) have been shown to enhance apoptosis of neutrophils and possess pro-resolution of inflammation properties. In order to search for new multi-target pro-resolution derivatives, here we describe the design, synthesis and investigation of the biological potential of a small series of hybrid compounds obtained by conjugating R-roscovitine with two different NO-donor moieties (compounds 2, 9a, 9c). The synthesized compounds were tested as potential pro-resolution agents, with their ability to promote human neutrophil apoptosis evaluated. Both compound 9a and 9c showed an increased pro-apoptotic activity when compared with either R-roscovitine or structurally related compounds devoid of the ability to release NO (des-NO analogues). Inhibition of either NO-synthase or soluble guanylate cyclase did not affect the induction of apoptosis by the R-roscovitine derivatives, similar to that reported for other classes of NO-donors. In contrast the NO scavenger PTIO prevented the enhanced apoptosis seen with compound 9a over R-roscovitine. These data show that novel compounds such as CDKi-NO-donor hybrids may have additive pro-resolution of inflammation effects. (C) 2013 Elsevier Ltd. All rights reserved.
• A Pd(0) based cross-coupling approach to the synthesis of 2-amidopurines and their evaluation as CDK inhibitors
  作者：Lucie Vandromme、Michel Legraverend、Sergio Kreimerman、Olivier Lozach、Laurent Meijer、David S. Grierson

  DOI：10.1016/j.bmc.2006.10.003

  日期：2007.1.1

  Two new series of 2-amido- and 2-aminocarbonylpurines have been synthesized using a Pd catalyst cross-coupling reaction either with amides or amines in the presence of CO. Moderate in vitro inhibitory activity against CDK1 and CDK5 was observed with IC50 of 0-9 mu M for the most active compound (18c). (c) 2006 Elsevier Ltd. All rights reserved.