(3R,4S,5S)-5-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino-4-methoxy-4-oxobutylthio)methyl)-tetrahydrofuran-2,3,4-triyl triacetate | 901776-32-7

• 分子结构分类: 有机化合物
• 英文名称: (3R,4S,5S)-5-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino-4-methoxy-4-oxobutylthio)methyl)-tetrahydrofuran-2,3,4-triyl triacetate
• 英文别名: methyl 2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[[(2S,3S,4R)-3,4,5-triacetyloxyoxolan-2-yl]methylsulfanyl]butanoate
• CAS: 901776-32-7
• 化学式: C₃₁H₃₅NO₁₁S
• 分子量: 629.685
• InChiKey: GBJRQABGRMAOBL-NIHBNWPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-5-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino-4-methoxy-4-oxobutylthio)methyl)-tetrahydrofuran-2,3,4-triyl triacetate 、 7-nitroimidazo[4,5-b]pyridine 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 2,6-二氯嘌呤 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 (2S,3S,4R,5R)-2-((3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-methoxy-4-oxobutylthio)methyl)-5-(7-nitro-3H-imidazo[4,5-b]pyridin-3-yl)tetrahydrofuran-3,4-diyl diacetate
  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：

  、 乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (3R,4S,5S)-5-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino-4-methoxy-4-oxobutylthio)methyl)-tetrahydrofuran-2,3,4-triyl triacetate
  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。
• INHIBITORS OF DNA METHYLTRANSFERASE
  申请人：Methylgene, Inc.

  公开号：EP1844062A2

  公开（公告）日：2007-10-17
• [EN] INHIBITORS OF DNA METHYLTRANSFERASE<br/>[FR] INHIBITEURS D'ADN-METHYLTRANSFERASE
  申请人：METHYLGENE INC

  公开号：WO2006078752A2

  公开（公告）日：2006-07-27

  [EN] The invention relates to the inhibition of DNA methyltransferase isoforms DNMT1 and DNMT3b2. The invention provides compounds and methods for inhibiting DNMT1 and DNMT3b2.
  [FR] L'invention concerne l'inhibition d'isoformes d'ADN-méthyltransférase DNMT1 et DNMT3b2. L'invention concerne des composés et des procédés permettant d'inhiber les isoformes DNMT1 et DNMT3b2.