2-phenyl-2,6-dihydro-furo[3,4-d][1,2,3]triazol-4-one | 73314-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-2,6-dihydro-furo[3,4-d][1,2,3]triazol-4-one
• 英文别名: 2-phenyl-5-hydroxymethyl-2H-1,2,3-triazole-4-carboxylic acid lactone；2-phenyl-2H-furo[3,4-d][1,2,3]triazol-4(6H)-one；2-phenyl-6H-furo[3,4-d]triazol-4-one
• CAS: 73314-46-2
• 化学式: C₁₀H₇N₃O₂
• 分子量: 201.184
• InChiKey: PAVOUWXAPOAUBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  盐酸胍 、 2-phenyl-2,6-dihydro-furo[3,4-d][1,2,3]triazol-4-one 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 sodium methylate 为溶剂， 生成 (2-Phenyl-5-hydroxymethyl-2H-1,2,3-triazole-4-carbonyl)guanidine hydrochloride
  参考文献：
  名称：

  N-[(substituted five-membered di- or triaza diunsaturated ring)carbonyl] guanidine derivatives for the treatment of ischemia

  摘要：

  NHE-1抑制剂，使用这种NHE-1抑制剂的方法以及含有这种NHE-1抑制剂的药物组合物。这些NHE-1抑制剂对于减少组织缺血引起的组织损伤是有用的。

  公开号：

  US06492401B1
• 作为产物：
  描述：

  furan-2,3,4-trione 3-oxime 4-phenylhydrazone 在 五氯化磷 作用下， 以 乙二醇二甲醚 为溶剂， 生成 2-phenyl-2,6-dihydro-furo[3,4-d][1,2,3]triazol-4-one
  参考文献：
  名称：

  Tetronic Acids and Derivatives; Part VI¹. A Convenient Synthesis of New 4-Oxo-2-phenyl-2H-4,6-dihydrofuro[3,4-d]triazole and 4-Oxo-4,6-dihydrofuro[3,4-c]furazan Systems

  摘要：

  DOI：

  10.1055/s-1979-28898

文献信息

• [EN] N-[(SUBSTITUTED FIVE-MEMBERED DI- OR TRIAZA DIUNSATURATED RING)CARBONYL] GUANIDINE DERIVATIVES FOR THE TREATMENT OF ISCHEMIA<br/>[FR] DERIVES DE LA N-[(A CYCLE DI OU TRIAZA DIINSATURE SUBSTITUE) CARBONYLE] GUANIDINE UTILISES POUR LE TRAITEMENT DE L'ISCHEMIE
  申请人：PFIZER PRODUCTS INC.

  公开号：WO1999043663A1

  公开（公告）日：1999-09-02

  (EN) NHE-1 inhibitors, methods of using such NHE-1 inhibitors and pharmaceutical compositions containing such NHE-1 inhibitors. The NHE-1 inhibitors are useful for the reduction of tissue damage resulting from tissue ischemia.(FR) L'invention porte sur des inhibiteurs du NHE-1, sur leurs procédés d'utilisation, et sur des préparations pharmaceutiques les contenant. Lesdits inhibiteurs servent à réduire les dommages tissulaires résultant de l'ischémie des tissus.

  NHE-1抑制剂，使用这种NHE-1抑制剂的方法以及含有这种NHE-1抑制剂的药物组合物。这些NHE-1抑制剂有助于减少组织缺血引起的组织损伤。
• N-[(substituted five-membered di-or triaza diunsaturated ring)carbonyl] guanidine derivatives for the treatment of ischemia
  申请人：Pfizer Inc.

  公开号：US20030149043A1

  公开（公告）日：2003-08-07

  NHE-1 inhibitors, methods of using such NHE-1 inhibitors and pharmaceutical compositions containing such NHE-1 inhibitors. The NHE-1 inhibitors are useful for the reduction of tissue damage resulting from tissue ischemia.

  NHE-1抑制剂，使用这种NHE-1抑制剂的方法以及含有这种NHE-1抑制剂的制药组合物。NHE-1抑制剂对于减少组织缺血引起的组织损伤是有用的。
• N-[(SUBSTITUTED FIVE-MEMBERED DI- OR TRIAZA DIUNSATURATED RING)CARBONYL]GUANIDINE DERIVATIVES FOR THE TREATMENT OF ISCHEMIA
  申请人：Pfizer Products Inc.

  公开号：EP1056729A1

  公开（公告）日：2000-12-06
• (S,R)-3-PHENYL-4,5 DIHYDRO-5-ISOXAZOLE ACETIC ACID-NITRIC OXIDE AND USE THEREOF AS ANTI-CANCER AND ANTIVIRAL AGENT
  申请人：Ganial Immunotherapeutics Inc.

  公开号：EP2144904A1

  公开（公告）日：2010-01-20
• (S,R.)-3-PHENYL-4,5 DIHYDRO-5-ISOXAZOLE ACETIC ACID-NITRIC OXIDE AND USE THEREOF AS ANTI-CANCER AND ANTIVIRAL AGENT
  申请人：Nicoletti Ferdinando

  公开号：US20100305176A1

  公开（公告）日：2010-12-02

  The present invention relates to an isoxazole derivative, the compound of formula (I) herein after referred to as GIT27-NO, which is the NO-donating structurally modified form of (S,R)-3-phenyl-4,5-dihydro-5-isoxazole acetic acid, herein after referred to as VGX-1027. Treatment of three tumor cell lines, rat astrocytoma C6, mouse fibrosarcoma L929, and mouse melanoma B16 cells with GIT27-NO resulted in a significant reduction of cell respiration and of number of viable cells, while VGX-1027 was completely ineffective. Hemoglobin, which act as NO-scavenger, restored cell viability, thus indicating the NO-mediated tumoricidal effect of compound (I). GIT27-NO triggered apoptotic cell death in L929 cell cultures, while autophagic cell death is mainly responsible for the diminished viability of C6 and B16 cells. Moreover, GIT27-NO induced the production of reactive oxygen species which can be neutralized by antioxidant N-acetyl cysteine (NAC), indicating that reactive oxygen species (ROS) are at least partly involved in the reduction of cell viability. The anti-tumor activity of GIT27-NO is mediated through activation of MAP kinases (ERK1/2, p38 and JNK) in cell-specific manner. The role of MAP kinases was further confirmed by specific inhibitors of these molecules, PD98059, SB202190, and SP600125. Finally, in vivo treatment with GIT27-NO significantly reduced tumor growth in syngeneic C57BL/6 mice implanted with B16 melanoma.