methyl 4-(((3aS,4S,6R,6aR)-6-(6-amino-2-methyl-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylthio)-2-(tert-butoxycarbonylamino)butanoate | 901776-48-5

• 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: methyl 4-(((3aS,4S,6R,6aR)-6-(6-amino-2-methyl-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylthio)-2-(tert-butoxycarbonylamino)butanoate
• 英文别名: methyl 4-[[(3aR,4R,6S,6aS)-4-(6-amino-2-methylpurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 901776-48-5
• 化学式: C₂₄H₃₆N₆O₇S
• 分子量: 552.652
• InChiKey: JUSJQCVEWDDLAZ-UEXBNONGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  187
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 4-(((3aS,4S,6R,6aR)-6-(6-amino-2-methyl-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylthio)-2-(tert-butoxycarbonylamino)butanoate 在 氢氧化钾 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  SAR around (l)-S-adenosyl-l-homocysteine, an inhibitor of human DNA methyltransferase (DNMT) enzymes

  摘要：

  The inhibitory activity of base-modified SAH analogues and the specificity of inhibiting human DNMT1 and DNMT3b2 enzymes was explored. The 6-amino group was essential while the 7-N of the adenine ring of SAH could be replaced by CH- without loss of activity against both enzymes. The introduction of small groups at the 2-position of the adenine moiety favors DNMT1 over DNMT3b2 inhibition whereas alkylation of the N-6-amino moiety favors the inhibition of DNMT3b2 enzyme. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.113
• 作为产物：
  描述：

  methyl 2-(R,S)-2-(tert-butoxycarbonylamino)-4-mercaptobutanoate 、 [(3aR,4R,6R,6aR)-4-(6-amino-2-methylpurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-methylbenzenesulfonate 以 甲醇 为溶剂， 反应 1.0h， 生成 methyl 4-(((3aS,4S,6R,6aR)-6-(6-amino-2-methyl-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylthio)-2-(tert-butoxycarbonylamino)butanoate
  参考文献：
  名称：

  SAR around (l)-S-adenosyl-l-homocysteine, an inhibitor of human DNA methyltransferase (DNMT) enzymes

  摘要：

  The inhibitory activity of base-modified SAH analogues and the specificity of inhibiting human DNMT1 and DNMT3b2 enzymes was explored. The 6-amino group was essential while the 7-N of the adenine ring of SAH could be replaced by CH- without loss of activity against both enzymes. The introduction of small groups at the 2-position of the adenine moiety favors DNMT1 over DNMT3b2 inhibition whereas alkylation of the N-6-amino moiety favors the inhibition of DNMT3b2 enzyme. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.113

文献信息

• Inhibitors of DNA Methyltransferase
  申请人：Wahhab Amal

  公开号：US20080132525A1

  公开（公告）日：2008-06-05

  The invention relates to the inhibition of DNA methyltransferase isoforms DNMT1 and DNMT3b2. The invention provides compounds and methods for inhibiting DNMT1 and DNMT3b2.

  这项发明涉及抑制DNA甲基转移酶亚型DNMT1和DNMT3b2。该发明提供了用于抑制DNMT1和DNMT3b2的化合物和方法。
• SAR around (l)-S-adenosyl-l-homocysteine, an inhibitor of human DNA methyltransferase (DNMT) enzymes
  作者：Oscar M. Saavedra、Ljubomir Isakovic、David B. Llewellyn、Lijie Zhan、Naomy Bernstein、Stephen Claridge、Franck Raeppel、Arkadii Vaisburg、Nadine Elowe、Andrea J. Petschner、Jubrail Rahil、Norman Beaulieu、A. Robert MacLeod、Daniel Delorme、Jeffrey M. Besterman、Amal Wahhab

  DOI：10.1016/j.bmcl.2009.03.113

  日期：2009.5

  The inhibitory activity of base-modified SAH analogues and the specificity of inhibiting human DNMT1 and DNMT3b2 enzymes was explored. The 6-amino group was essential while the 7-N of the adenine ring of SAH could be replaced by CH- without loss of activity against both enzymes. The introduction of small groups at the 2-position of the adenine moiety favors DNMT1 over DNMT3b2 inhibition whereas alkylation of the N-6-amino moiety favors the inhibition of DNMT3b2 enzyme. (C) 2009 Elsevier Ltd. All rights reserved.