2-acetyl-7-carboxymethyloxy-4-carboxymethylsulfamoylbenzofuran | 105642-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-acetyl-7-carboxymethyloxy-4-carboxymethylsulfamoylbenzofuran
• 英文别名: 2-acetyl-4-(N-carboxymethylsulfamoyl)-7-(carboxymethoxy)benzofuran；2-[[2-Acetyl-7-(carboxymethoxy)-1-benzofuran-4-yl]sulfonylamino]acetic acid
• CAS: 105642-00-0
• 化学式: C₁₄H₁₃NO₉S
• 分子量: 371.325
• InChiKey: JLTWKPUKXNDBPG-UHFFFAOYSA-N

物化性质

• 沸点：
  666.0±65.0 °C(Predicted)
• 密度：
  1.581±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-乙酰-7-羟基苯并呋喃 在 氯磺酸 、 sodium hydroxide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 23.0h， 生成 2-acetyl-7-carboxymethyloxy-4-carboxymethylsulfamoylbenzofuran
  参考文献：
  名称：

  Synthesis and aldose reductase-inhibitory activity of benzo(b)furan derivatives possessing a carboxymethylsulfamoyl group.

  摘要：

  合成了多种含有羧甲基磺酰胺基团的苯并[b]呋喃衍生物，并对其对醛糖还原酶的抑制活性进行了评估。大多数化合物表现出显著的抑制活性（IC50，10^-8-10^-7M）。在测试的化合物中，位于3位或4位的羧甲基磺酰胺基团的化合物表现出最强的抑制活性。讨论了测试化合物的结构-活性趋势。

  DOI：

  10.1248/cpb.37.2398

文献信息

• Benzofuran derivatives useful in treating diabetic complications
  申请人：Kaken Pharmaceutical Co., Ltd.

  公开号：US04666931A1

  公开（公告）日：1987-05-19

  A benzofuran derivative having the general formula (I): ##STR1## wherein R.sup.1 is hydrogen atom, a benzyl group, unsubstituted or substituted with a halogen atom or an alkyloxy group, or an alkyl group having 1 to 3 carbon atoms, R.sup.2 is hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R.sup.3 is acetyl group, ethyl group, carboxyl group or 4-methyl-2,5-dioxoimidazolidine-4-yl group, R.sup.4 is hydrogen atom, hydroxyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, carboxymethoxy group, nitro group, acetoamino group, a benzylozy group unsubstituted or substituted with a halogen atom, nitro group or an alkyloxy group or a group having the formula: --OR.sup.6, wherein R.sup.6 is an alkenyl group having 2 to 4 carbon atoms or an alkyl group having 2 to 3 carbon atoms having a halogen atom, cyano group or oxo group, R.sup.5 is hydrogen atom or methylenedioxy group together with R.sup.4 group, n is 1 or 2, and the unsubstituted or substituted N-carboxymethylsulfamoyl group, R.sup.4 and R.sup.5 are attached at 3-position, 4-position, 5-position, 6-position or 7-position of the benzofuran ring, or a nontoxic salt thereof, process for preparing the same and a pharmaceutical composition containing the same. The compounds of the present invention have powerful aldose reductase inhibiting activity, platelet aggregation inhibiting activity and arachidonic acid metabolism inhibiting activity and are useful for a remedy for treatment of diabetic complications.

  一种具有通式（I）的苯并呋喃衍生物：##STR1## 其中R.sup.1是氢原子，苄基，未取代或取代有卤原子或烷氧基的苄基，或具有1至3个碳原子的烷基基团，R.sup.2是氢原子或具有1至3个碳原子的烷基基团，R.sup.3是乙酰基，乙基基团，羧基或4-甲基-2,5-二氧代咪唑烷-4-基团，R.sup.4是氢原子，羟基，具有1至6个碳原子的烷基基团，具有1至9个碳原子的烷氧基团，羧甲氧基基团，硝基基团，乙酰氨基基团，未取代或取代有卤原子、硝基基团或烷氧基的苄氧基基团或具有以下式的基团：--OR.sup.6，其中R.sup.6是具有2至4个碳原子的烯基基团或具有2至3个碳原子的烷基基团，带有卤原子、氰基团或氧代基，R.sup.5是氢原子或与R.sup.4基团一起的亚甲二氧基基团，n为1或2，并且未取代或取代的N-羧甲基磺胺基团，R.sup.4和R.sup.5连接在苯并呋喃环的3位、4位、5位、6位或7位，或其无毒盐，制备该化合物的方法以及含有该化合物的药物组合物。本发明的化合物具有强大的醛糖还原酶抑制活性、血小板聚集抑制活性和花生四烯酸代谢抑制活性，并可用于治疗糖尿病并发症的治疗方法。
• Benzofuran derivative, process for preparing the same and pharmaceutical composition containing the same
  申请人：Kaken Pharmaceutical Co., Ltd.

  公开号：EP0187387A1

  公开（公告）日：1986-07-16

  A benzofuran derivative having the general formula (I): wherein R' is hydrogen atom, a benzyl group, unsubstituted or substituted with a halogen atom or an alkyloxy group, or an alkyl group having 1 to 3 carbon atoms, R2 is hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R' is acetyl group, ethy group, carboxyl group or 4-methyl-2,5-dioxoimidazcrndine-4-yl group, R4 is hydrogen atom, hydroxyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, carboxymethoxy group, nitro group, acetoamino group, a benzyloxy group unsubstituted or substituted with a halogen atom, nitro group or an alkyloxy group or a group having the formula: -OR6, wherein R6 is an alkenyl group having 2 to 4 carbon atoms or an alkyl group having 2 to 3 carbon atoms having a halogen atom, cyano group or oxo group, R5 is hydrogen atom or methylenedioxy group together with R4 group, n is 1 or 2, and the unsubstituted or substituted N-carboxymethylsulfamoyl group, R4 and R5 are attached at 3-position, 4-position, 5-position, 6-position or 7-position of the benzofuran ring, or a nontoxic salt thereof, process for preparing the same and a parmaceutical composition containing the same. The compounds of the present invention have powerful aldoe reductase inhibiting activity, platelet aggregation inhibiting activity and arachidonic acid metabolism inhibiting activity and are useful for a remedy for treatment of diabetic complication.

  具有通式(I)的苯并呋喃衍生物： 其中 R'是氢原子、未取代或被卤素原子或烷氧基取代的苄基或具有 1 至 3 个碳原子的烷基，R2 是氢原子或具有 1 至 3 个碳原子的烷基，R'是乙酰基、乙基、羧基或 4-甲基-2,5-二氧代咪唑啉-4-基、R4 是氢原子、羟基、具有 1 至 6 个碳原子的烷基、具有 1 至 9 个碳原子的烷氧基、羧基甲氧基、硝基、乙酰氨基、未取代或被卤素原子取代的苄氧基、硝基或烷氧基或具有以下式子的基团：-OR6，其中 R6 是具有 2 至 4 个碳原子的烯基或具有 2 至 3 个碳原子并带有卤素原子、氰基或氧基的烷基，R5 是氢原子或与 R4 一起的亚甲基二氧基，n 是 1 或 2、和未取代或取代的 N-羧甲基氨基磺酰基，R4 和 R5 连接在苯并呋喃环的 3-位、4-位、5-位、6-位或 7-位，或其无毒盐，以及制备方法和含有上述物质的药物组合物。 本发明的化合物具有强大的醛还原酶抑制活性、血小板聚集抑制活性和花生四烯酸代谢抑制活性，可用于治疗糖尿病并发症。
• OHISHI, YOSHITAKA;MUKAI, TERUO;NAGAHARA, MICHIKO;YAJIMA, MOTOYUKI;KAJIKAW+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2398-2405
  作者：OHISHI, YOSHITAKA、MUKAI, TERUO、NAGAHARA, MICHIKO、YAJIMA, MOTOYUKI、KAJIKAW+

  DOI：——

  日期：——
• Synthesis and aldose reductase-inhibitory activity of benzo(b)furan derivatives possessing a carboxymethylsulfamoyl group.
  作者：Yoshitaka OHISHI、Teruo MUKAI、Michiko NAGAHARA、Motoyuki YAJIMA、Norio KAJIKAWA

  DOI：10.1248/cpb.37.2398

  日期：——

  Various benzo[b]futran derivatives with a carboxymethylsulfamoyl group were prepared and evaluated for aldose reductase-inhibitory potency. Most of the compounds displayed significant inhibitory activities (IC50, 10-8-10-7M). Among the test compounds, the compounds having a carboxymethylsulfamoyl group at the 3- or 4-position exhibited the greatest inhibitory potency. Structure-activity trends of the tested compounds are discussed.

  合成了多种含有羧甲基磺酰胺基团的苯并[b]呋喃衍生物，并对其对醛糖还原酶的抑制活性进行了评估。大多数化合物表现出显著的抑制活性（IC50，10^-8-10^-7M）。在测试的化合物中，位于3位或4位的羧甲基磺酰胺基团的化合物表现出最强的抑制活性。讨论了测试化合物的结构-活性趋势。