methyl 3-(4-pentylphenylethynyl)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,4]triazole-5-carboxylate | 1190605-20-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: methyl 3-(4-pentylphenylethynyl)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,4]triazole-5-carboxylate
• 英文别名: methyl 2-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-5-[2-(4-pentylphenyl)ethynyl]-1,2,4-triazole-3-carboxylate
• CAS: 1190605-20-9
• 化学式: C₂₈H₃₃N₃O₉
• 分子量: 555.585
• InChiKey: IFIHCBOBBAHVIG-LYPBTDJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-pentylphenylethynyl)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,4]triazole-5-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以71%的产率得到
  参考文献：
  名称：

  Novel Triazole Ribonucleoside Down-Regulates Heat Shock Protein 27 and Induces Potent Anticancer Activity on Drug-Resistant Pancreatic Cancer

  摘要：

  A series of novel 3-arylethynyltriazolyl ribonucleosides were synthesized and assessed for their anticancer activity on the drug-resistant pancreatic cancer cell line MiaPaCa-2. Among them, one compound exhibited potent apoptosis-inducing properties and anticancer activity against the pancreatic cancer model MiaPaCa-2 both in vitro and in vivo with no adverse effects. This compound did not inhibit DNA synthesis and therefore does not resemble the clinical drug gemcitabine. It did, however, significantly down-regulate the expression of heat shock protein 27 (Hsp27), a small molecular chaperone playing an important role in drug resistance and highly expressed in drug-resistant cancer forms, and thus represents the first small molecular anticancer lead with such a mode of action.

  DOI：

  10.1021/jm900960v
• 作为产物：
  描述：

  4-戊基苯乙炔 、 3-bromo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-5-carboxylic acid methyl ester 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以73%的产率得到methyl 3-(4-pentylphenylethynyl)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,4]triazole-5-carboxylate
  参考文献：
  名称：

  Novel Triazole Ribonucleoside Down-Regulates Heat Shock Protein 27 and Induces Potent Anticancer Activity on Drug-Resistant Pancreatic Cancer

  摘要：

  A series of novel 3-arylethynyltriazolyl ribonucleosides were synthesized and assessed for their anticancer activity on the drug-resistant pancreatic cancer cell line MiaPaCa-2. Among them, one compound exhibited potent apoptosis-inducing properties and anticancer activity against the pancreatic cancer model MiaPaCa-2 both in vitro and in vivo with no adverse effects. This compound did not inhibit DNA synthesis and therefore does not resemble the clinical drug gemcitabine. It did, however, significantly down-regulate the expression of heat shock protein 27 (Hsp27), a small molecular chaperone playing an important role in drug resistance and highly expressed in drug-resistant cancer forms, and thus represents the first small molecular anticancer lead with such a mode of action.

  DOI：

  10.1021/jm900960v

文献信息

• Novel triazole nucleoside derivatives, their preparation and their application in therapeutics
  申请人：INSERM (Institut National de la Santé et de la Recherche Medicale)

  公开号：EP2113508A1

  公开（公告）日：2009-11-04

  The present invention relates to novel compound of formula (I): in the form of a free base or of an addition salt with an acid. The invention also relates to process of preparation of compounds of formula (I), to composition comprising them and to their application in therapeutics and in particular in cancers.

  本发明涉及一种新的化合物，其化学式为(I)，可以是自由碱或与酸形成的加成盐。本发明还涉及制备化合物(I)的方法，包括含有它们的组合物以及它们在治疗学中的应用，特别是在癌症治疗中的应用。
• NOVEL TRIAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS
  申请人：Inserm Transfert

  公开号：EP2279193A1

  公开（公告）日：2011-02-02
• US8563526B2
  申请人：——

  公开号：US8563526B2

  公开（公告）日：2013-10-22
• [EN] NOVEL TRIAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS<br/>[FR] NOUVEAUX DÉRIVÉS DE TRIAZOLE, LEUR PRÉPARATION ET LEUR APPLICATION EN THÉRAPEUTIQUE
  申请人：INSERM TRANSFERT

  公开号：WO2009133147A1

  公开（公告）日：2009-11-05

  The present invention relates to novel compounds of formula (A): in the form of a free base or of an addition salt with an acid. The invention also relates to process of preparation of compounds of formula (A), to composition comprising them and to their application in therapeutics and in particular in cancers.
• Novel Triazole Ribonucleoside Down-Regulates Heat Shock Protein 27 and Induces Potent Anticancer Activity on Drug-Resistant Pancreatic Cancer
  作者：Yi Xia、Yang Liu、Jinqiao Wan、Menghua Wang、Palma Rocchi、Fanqi Qu、Juan L. Iovanna、Ling Peng

  DOI：10.1021/jm900960v

  日期：2009.10.8

  A series of novel 3-arylethynyltriazolyl ribonucleosides were synthesized and assessed for their anticancer activity on the drug-resistant pancreatic cancer cell line MiaPaCa-2. Among them, one compound exhibited potent apoptosis-inducing properties and anticancer activity against the pancreatic cancer model MiaPaCa-2 both in vitro and in vivo with no adverse effects. This compound did not inhibit DNA synthesis and therefore does not resemble the clinical drug gemcitabine. It did, however, significantly down-regulate the expression of heat shock protein 27 (Hsp27), a small molecular chaperone playing an important role in drug resistance and highly expressed in drug-resistant cancer forms, and thus represents the first small molecular anticancer lead with such a mode of action.