5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1-<5-(morpholinocarbonyl)pentyl>indole | 129423-44-5

• 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: 5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1-<5-(morpholinocarbonyl)pentyl>indole
• 英文别名: 6-[5-hydroxy-2-(4-hydroxyphenyl)-3-methylindol-1-yl]-1-morpholin-4-ylhexan-1-one
• CAS: 129423-44-5
• 化学式: C₂₅H₃₀N₂O₄
• 分子量: 422.524
• InChiKey: VUNCLVUDXCCVKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.93
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1-<5-(morpholinocarbonyl)pentyl>indole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以43%的产率得到2-(4-Hydroxyphenyl)-3-methyl-1-(6-morpholin-4-ylhexyl)indol-5-ol
  参考文献：
  名称：

  1-(Aminoalkyl)-2-phenylindoles as novel pure estrogen antagonists

  摘要：

  A number of 1-(omega-aminoalkyl)-5-hydroxy-2-(4-hydroxyphenyl)indoles were synthesized and studied for their binding affinities for the calf uterine estrogen receptor and estrogen antagonistic activities. Highest binding affinities were found with derivatives bearing a methyl group in position 3 and a hexamethylene chain between the indole and amino nitrogen atoms. Values for relative binding affinity (RBA) are between 20 and 30 for derivatives 5b, 5c, 5f, and 5h (17 beta-estradiol = 100). In the mouse uterine weight test, no significant agonistic (estrogenic) activity was observed up to a daily dose of 125 micrograms/animal, except for derivatives 5c, 5j, and 5l. 2-Phenylindoles with amino (5b), pyrrolidino (5f), piperidino (5h), and morpholino (5k) groups as the amino function completely suppressed estrone-stimulated uterine growth as a dose of 125 micrograms/animal (100% antagonism). Therefore, these derivatives can be considered as first examples of nonsteroidal pure antiestrogens.

  DOI：

  10.1021/jm00171a045
• 作为产物：
  描述：

  5-甲氧基-2-(4-甲氧基苯基)-3-甲基-1H-吲哚 在 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 4.33h， 生成 5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1-<5-(morpholinocarbonyl)pentyl>indole
  参考文献：
  名称：

  1-(Aminoalkyl)-2-phenylindoles as novel pure estrogen antagonists

  摘要：

  A number of 1-(omega-aminoalkyl)-5-hydroxy-2-(4-hydroxyphenyl)indoles were synthesized and studied for their binding affinities for the calf uterine estrogen receptor and estrogen antagonistic activities. Highest binding affinities were found with derivatives bearing a methyl group in position 3 and a hexamethylene chain between the indole and amino nitrogen atoms. Values for relative binding affinity (RBA) are between 20 and 30 for derivatives 5b, 5c, 5f, and 5h (17 beta-estradiol = 100). In the mouse uterine weight test, no significant agonistic (estrogenic) activity was observed up to a daily dose of 125 micrograms/animal, except for derivatives 5c, 5j, and 5l. 2-Phenylindoles with amino (5b), pyrrolidino (5f), piperidino (5h), and morpholino (5k) groups as the amino function completely suppressed estrone-stimulated uterine growth as a dose of 125 micrograms/animal (100% antagonism). Therefore, these derivatives can be considered as first examples of nonsteroidal pure antiestrogens.

  DOI：

  10.1021/jm00171a045

文献信息

• VON, ANGERER ERWIN;KNEBEL, NORBERT;KAGER, MARIO;GANSS, BERNHARD, J. MED. CHEM., 33,(1990) N, C. 2635-2640
  作者：VON, ANGERER ERWIN、KNEBEL, NORBERT、KAGER, MARIO、GANSS, BERNHARD

  DOI：——

  日期：——