[6-methyl-5-(3-phenyl-acryloyl)-5H-[1,3]dioxolo[4,5-f]indol-7-yl]-acetic acid | 37646-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [6-methyl-5-(3-phenyl-acryloyl)-5H-[1,3]dioxolo[4,5-f]indol-7-yl]-acetic acid
• 英文别名: 2-[6-Methyl-5-(3-phenylprop-2-enoyl)-[1,3]dioxolo[4,5-f]indol-7-yl]acetic acid
• CAS: 37646-31-4
• 化学式: C₂₁H₁₇NO₅
• 分子量: 363.37
• InChiKey: BAOWVODWXXCRBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  sodium N1-cinnamoyl-3,4-methylenedioxyphenylhydrazine N2 sulfite 、 乙酰丙酸 以 水 为溶剂， 反应 3.0h， 以to give 1-cinnamoyl-2-methyl-5,6-methylenedioxy-3-indolylacetic acid的产率得到[6-methyl-5-(3-phenyl-acryloyl)-5H-[1,3]dioxolo[4,5-f]indol-7-yl]-acetic acid
  参考文献：
  名称：

  Novel N'-acylated phenyl-hydrazine and hydrozone derivatives

  摘要：

  具有出色的抗炎、退烧和镇痛活性的新型吲哚乙酸衍生物，其化学式如下：##SPC1##其中X.sub.1和X.sub.2分别是从氧和亚甲基组成的群体中选择的成员；A是从具有高达5个碳原子的未取代饱和碳氢链、具有高达5个碳原子的未取代不饱和碳氢链和具有高达5个碳原子的取代饱和或取代乙烯不饱和碳氢链中选择的成员，其中取代基选择自卤素或苯基，碳氢链是直链或分枝的；m为0或1；n为1或2；R.sub.1和R.sub.2分别是从氢和具有高达4个碳原子的烷基中选择的成员；R.sub.3是从具有高达4个碳原子的烷基、未取代或低级烷氧基、低级烷基硫基、硝基、氰基、亚甲二氧基、乙二氧基或卤素取代的芳基中选择的成员，每个烷基、烷氧基和烷基硫基取代基含有高达4个碳原子，或未取代、卤素、烷基或苯基取代的或苯环共轭的、饱和或不饱和的单环或多环脂环基，或由该脂环基取代的烷基基团，或未取代或甲基、乙基或卤素取代的含氧、硫或氮原子的5-或6-成员杂环环基；R.sub.4是从具有高达4个碳原子的烷基或氢中选择的成员，或M（其中M是阳离子）的一个基团。公式（I）的吲哚乙酸是通过将公式如下的化合物：##SPC2##其中X.sub.1、X.sub.2和n与上述定义相同，B是从##EQU1##和Z（其中Z是包含至少一个容易去除的基团的氮保护系统）的群体中选择的成员，与代表公式的酸卤化物反应得到公式的N.sup.1-酰化化合物：##SPC3##其中X.sub.1、X.sub.2、R.sub.3、A、B、m和n与上述定义相同，然后将所得的N.sup.1-酰化化合物（II）与代表公式的脂肪酸衍生物反应：##EQU2##其中R.sub.1、R.sub.2和R.sub.4与上述定义相同。

  公开号：

  US03974145A1

文献信息

• Komatsu; Awata; Sakai, Arzneimittel-Forschung/Drug Research, 1972, vol. 22, # 12, p. 2099 - 2104
  作者：Komatsu、Awata、Sakai、Inukai、Kimura、Inaba、Yamamoto

  DOI：——

  日期：——
• Novel N'-acylated phenyl-hydrazine and hydrozone derivatives
  申请人：Sumitomo Chemical Company, Limited

  公开号：US03974145A1

  公开（公告）日：1976-08-10

  Novel indolylacetic acid derivatives, which have excellent anti-inflammatory, antipyretic and analgesic activities, represented by the formula, ##SPC1## Wherein X.sub.1 and X.sub.2 each is a member selected from the group consisting of oxygen and methylene; A is a member selected from the group consisting of unsubstituted saturated hydrocarbon chain having up to 5 carbon atoms, unsubstituted unsaturated hydrocarbon chain having up to 5 carbon atoms and substituted saturated or substituted ethylenically unsaturated hydrocarbon chain having up to 5 carbon atoms, in which the substituents are selected from the group consisting of halogen or phenyl, the hydrocarbon chain being straight or blanched one; m is 0 or 1; n is 1 or 2; R.sub.1 and R.sub.2 each is a member selected from the group consisting of hydrogen and alkyl having up to 4 carbon atoms; R.sub.3 is a member selected from the group consisting of alkyl having up to 4 carbon atoms, unsubstituted or a lower alkyl-, lower alkoxy-, lower alkylthio-, nitro-, cyano-, methylenedioxy-, ethylenedioxy- or halogen-substituted aryl, each of said alkyl, alkoxy and alkylthio substituents containing up to 4 carbon atoms, or unsubstituted, or halogen-, alkyl- or phenyl-substituted or benzene ring-condensed, saturated or unsaturated mono- or poly-aclicyclic group, or alkyl group substituted by said alicyclic group, or unsubstituted or methyl-, ethyl- or halogen-substituted 5- or 6-membered heterocyclic ring group containing oxygen, sulfur or nitrogen atom; R.sub.4 is a member selected from the group consisting of alkyl having up to 4 carbon atoms or hydrogen, or a group of M (wherein M is a cation). The indolylacetic acid of the formula (I) is prepared by reacting a compound of the formula, ##SPC2## Wherein X.sub.1, X.sub.2 and n are the same as defined above and B is a member selected from the group consisting of ##EQU1## and Z (wherein Z is a nitrogen protecting system comprising at least one readily removable group), with an acid halide represented by the formula, R.sub.3 --(A).sub.m --CO--hal (V) wherein R.sub.3, A and m are the same as defined above and hal is halogen, to obtain N.sup.1 -acylated compound of the formula, ##SPC3## Wherein X.sub.1, X.sub.2, R.sub.3, A, B, m and n are the same as defined above, then reacting the resultant N.sup.1 -acylated compound (II) with an aliphatic acid derivative represented by the formula, ##EQU2## wherein R.sub.1, R.sub.2 and R.sub.4 are the same as defined above.

  具有出色的抗炎、退烧和镇痛活性的新型吲哚乙酸衍生物，其化学式如下：##SPC1##其中X.sub.1和X.sub.2分别是从氧和亚甲基组成的群体中选择的成员；A是从具有高达5个碳原子的未取代饱和碳氢链、具有高达5个碳原子的未取代不饱和碳氢链和具有高达5个碳原子的取代饱和或取代乙烯不饱和碳氢链中选择的成员，其中取代基选择自卤素或苯基，碳氢链是直链或分枝的；m为0或1；n为1或2；R.sub.1和R.sub.2分别是从氢和具有高达4个碳原子的烷基中选择的成员；R.sub.3是从具有高达4个碳原子的烷基、未取代或低级烷氧基、低级烷基硫基、硝基、氰基、亚甲二氧基、乙二氧基或卤素取代的芳基中选择的成员，每个烷基、烷氧基和烷基硫基取代基含有高达4个碳原子，或未取代、卤素、烷基或苯基取代的或苯环共轭的、饱和或不饱和的单环或多环脂环基，或由该脂环基取代的烷基基团，或未取代或甲基、乙基或卤素取代的含氧、硫或氮原子的5-或6-成员杂环环基；R.sub.4是从具有高达4个碳原子的烷基或氢中选择的成员，或M（其中M是阳离子）的一个基团。公式（I）的吲哚乙酸是通过将公式如下的化合物：##SPC2##其中X.sub.1、X.sub.2和n与上述定义相同，B是从##EQU1##和Z（其中Z是包含至少一个容易去除的基团的氮保护系统）的群体中选择的成员，与代表公式的酸卤化物反应得到公式的N.sup.1-酰化化合物：##SPC3##其中X.sub.1、X.sub.2、R.sub.3、A、B、m和n与上述定义相同，然后将所得的N.sup.1-酰化化合物（II）与代表公式的脂肪酸衍生物反应：##EQU2##其中R.sub.1、R.sub.2和R.sub.4与上述定义相同。