1,3-苯并二氧戊环-4,5-二胺 | 500862-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 1,3-苯并二氧戊环-4,5-二胺
• 英文名称: benzo[1,3]dioxole-4,5-diyldiamine
• 英文别名: Benzo[1,3]dioxol-4,5-diyldiamin；1,3-Benzodioxole-4,5-diamine
• CAS: 500862-27-1
• 化学式: C₇H₈N₂O₂
• mdl: MFCD18805481
• 分子量: 152.153
• InChiKey: WZXFIDXRXIOGTR-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  331.7±42.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-苯并二氧戊环-4,5-二胺 在 盐酸 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 6-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-7-(difluoromethyl)-6H-[1,3]dioxolo[4,5-e]benzimidazole
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Analogues of the Pan Class I Phosphatidylinositol 3-Kinase (PI3K) Inhibitor 2-(Difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474)

  摘要：

  A structure activity relationship (SAR) study of the pan class I PI 3-kinase inhibitor 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474) identified substitution at the 4 and 6 positions of the benzimidazole ring as having significant effects on the potency of substituted derivatives. The 6-amino-4-methoxy analogue displayed a greater than 1000-fold potency enhancement over the corresponding 6-aza-4-methoxy analogue against all three class Ia PI 3-kinase enzymes (p110 alpha, p110 beta, and p110 delta) and also displayed significant potency against two mutant forms of the p110 alpha isoform (H1047R and E545K). This compound was also evaluated in vivo against a U87MG human glioblastoma tumor xenograft model in Ragl(-/-) mice, and at a dose of 50 mg/kg given by ip injection at a qd x 10 dosing schedule it dramatically reduced cancer growth by 81% compared to untreated controls.

  DOI：

  10.1021/jm200688y
• 作为产物：
  描述：

  3-硝基-1,2-苯二醇 在 tin(II) chloride dihdyrate 、 potassium carbonate 、 copper(II) oxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1,3-苯并二氧戊环-4,5-二胺
  参考文献：
  名称：

  一类抑制丙肝病毒的大环状杂环化合物及其 制备和用途

  摘要：

  本申请涉及一类抑制HCV的化合物，所述化合物由式A表示。本申请还涉及该类化合物的制备和制药用途。

  公开号：

  CN107074876B

文献信息

• Pyrimido[1,2-a ]benzimidazole derivatives
  申请人：Imperial Chemical Industries Limited

  公开号：US04167569A1

  公开（公告）日：1979-09-11

  The invention concerns 3,4-dihydropyrimido [1,2-a]benzimidazole derivatives bearing one or more substituents at positions 6, 7, 8 or 9; processes for their preparation and manufacture; and pharmaceutical compositions thereof. The compounds inhibit the aggregation of blood-platelets and may be used in vivo, in the treatment or prophylaxis of thrombosis or occlusive vascular disease, or in vitro, in helping to stabilize preparations of blood platelets. Representative compounds of the invention are 7- and 8- acetyl-3,4-dihydropyrimido[1,2-a]benzimidazol-2(1H)-one.

  本发明涉及在6、7、8或9位带有一个或多个取代基的3,4-二氢嘧啶并[1,2-a]苯并咪唑衍生物；它们的制备和制造过程；以及它们的制药组合物。这些化合物能够抑制血小板的聚集，可以在体内用于治疗或预防血栓形成或闭塞性血管疾病，也可以在体外用于帮助稳定血小板制剂。本发明的代表化合物是7-和8-乙酰基-3,4-二氢嘧啶并[1,2-a]苯并咪唑-2(1H)-酮。
• Behavior of Piperonal Derivatives toward Bromination and Nitration¹
  作者：L. Chas. Raiford、Fred W. Oberst

  DOI：10.1021/ja01337a071

  日期：1933.10
• US4167569A
  申请人：——

  公开号：US4167569A

  公开（公告）日：1979-09-11
• 一类抑制丙肝病毒的大环状杂环化合物及其 制备和用途
  申请人：上海长森药业有限公司

  公开号：CN107074876B

  公开（公告）日：2019-12-20

  本申请涉及一类抑制HCV的化合物，所述化合物由式A表示。本申请还涉及该类化合物的制备和制药用途。
• Synthesis and Biological Evaluation of Novel Analogues of the Pan Class I Phosphatidylinositol 3-Kinase (PI3K) Inhibitor 2-(Difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1<i>H</i>-benzimidazole (ZSTK474)
  作者：Gordon W. Rewcastle、Swarna A. Gamage、Jack U. Flanagan、Raphael Frederick、William A. Denny、Bruce C. Baguley、Philip Kestell、Ripudaman Singh、Jackie D. Kendall、Elaine S. Marshall、Claire L. Lill、Woo-Jeong Lee、Sharada Kolekar、Christina M. Buchanan、Stephen M. F. Jamieson、Peter R. Shepherd

  DOI：10.1021/jm200688y

  日期：2011.10.27

  A structure activity relationship (SAR) study of the pan class I PI 3-kinase inhibitor 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474) identified substitution at the 4 and 6 positions of the benzimidazole ring as having significant effects on the potency of substituted derivatives. The 6-amino-4-methoxy analogue displayed a greater than 1000-fold potency enhancement over the corresponding 6-aza-4-methoxy analogue against all three class Ia PI 3-kinase enzymes (p110 alpha, p110 beta, and p110 delta) and also displayed significant potency against two mutant forms of the p110 alpha isoform (H1047R and E545K). This compound was also evaluated in vivo against a U87MG human glioblastoma tumor xenograft model in Ragl(-/-) mice, and at a dose of 50 mg/kg given by ip injection at a qd x 10 dosing schedule it dramatically reduced cancer growth by 81% compared to untreated controls.