(-)-N¹-phenethylnoreseromethole | 114546-56-4

• 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: (-)-N¹-phenethylnoreseromethole
• 英文别名: (3AS-cis)-1,2,3,3a,8,8a-hexahydro-5-methoxy-1-(2-phenylethyl)-3a,8-dimethylpyrrolo[2,3-b]indole；(3aR,8bS)-7-methoxy-4,8b-dimethyl-3-(2-phenylethyl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole
• CAS: 114546-56-4
• 化学式: C₂₁H₂₆N₂O
• 分子量: 322.45
• InChiKey: RSTJEINPEJMSDR-SFTDATJTSA-N

物化性质

• 沸点：
  462.4±45.0 °C(predicted)
• 密度：
  1.104±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-N¹-phenethylnoreseromethole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到(-)-N¹-phenethylnoreseroline
  参考文献：
  名称：

  Pei, Xue-Feng; Greig, Nigel H.; Bi, Sheng, Medicinal Chemistry Research, 1995, vol. 5, # 6, p. 455 - 461

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-N¹-noresermethole 、 (1-溴乙基)苯 以 N-甲基乙酰胺 、 水 为溶剂， 生成 (-)-N¹-phenethylnoreseromethole
  参考文献：
  名称：

  Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and)

  摘要：

  描述了以下化合物的化学式##STR1## 其中（a）X为O或S；（b）R为H、loweralkyl、##STR2## 其中Y为O或S；R.sub.2为烷基、环烷基、双环烷基、环烯基、芳基、芳基loweralkyl、杂环芳基或杂环芳基loweralkyl，R.sub.3为H或烷基，或整体视为--NR.sub.2 R.sub.3时为1-吡咯基、1-哌啶基、4-吗啉基、4-硫代吗啉基、1-哌嗪基、4-甲基-1-哌嗪基或2-(2,6-二氯苯基亚胺基)-1-咪唑烷基）和R.sub.4为氢、loweralkyl、芳基loweralkyl、二芳基loweralkyl、芳基或杂环芳基，（c）m为1或2；（d）每个Z独立地为H、loweralkyl、卤素、硝基、--NH.sub.2、loweralkylcarbonylamino、arylcarbonylamino、loweralkoxycarbonylamino或loweralkylamino，（e）R.sub.1为H、loweralkyl、芳基loweralkyl、杂环芳基loweralkyl、环烷基甲基或loweralkenylmethyl，但当X为O时，m为1、Z为H且R.sub.1为甲基时，R不是--CONHCH.sub.3、--CONHC.sub.6 H.sub.5、氢、甲基或乙基，当X为O时，m为1且Z和R.sub.1均为氢时，R不是氢或甲基，以及其药用可接受的酸盐，可用作增强记忆和镇痛剂。

  公开号：

  US04791107A1

文献信息

• Method for preparing 1, 2, 3, 3A, 8, 8A-hexahydro-3A, 8 (and 1, 3A,
  申请人：Hoechst Marion Roussel, Inc.

  公开号：US05621114A1

  公开（公告）日：1997-04-15

  There are described compounds of the formula ##STR1## where (a) X is O or S; (b) R is H, loweralkyl, ##STR2## where Y is O or S; R.sub.2 is alkyl, cycloalkyl, bicycloalkyl, cycloalkenyl, aryl, arylloweralkyl, heteroaryl or heteroarylloweralkyl, R.sub.3 is H or alkyl, or the group --NR.sub.2 R.sub.3 taken as a whole is 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl or 2-(2,6-dichlorophenylimino)-1-imidazolidinyl) and R.sub.4 is hydrogen, loweralkyl, arylloweralkyl, diarylloweralkyl, aryl or heteroaryl, (c) m is 1 or 2; (d) each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino, and (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heteroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, with the proviso that when X is O, m is 1, Z is H and R.sub.1 is methyl, R is not --CONHCH.sub.3, --CONHC.sub.6 H.sub.5, hydrogen, methyl or ethyl, and that when X is O, m is 1 and Z and R.sub.1 are both hydrogen, R is not hydrogen or methyl, and pharmaceutically acceptable acid addition salts thereof which are useful as memory-enhancing and analgesic agents.

  描述了一种化合物的公式 ##STR1## 其中：(a) X为O或S; (b) R为H、低烷基、##STR2## 其中Y为O或S; R.sub.2为烷基、环烷基、双环烷基、环烯基、芳基、芳基低烷基、杂环芳基或杂环芳基低烷基，R.sub.3为H或烷基，或作为整体的--NR.sub.2R.sub.3为1-吡咯基、1-哌啶基、4-吗啉基、4-硫代吗啉基、1-哌嗪基、4-甲基-1-哌嗪基或2-(2,6-二氯苯基亚氨基)-1-咪唑啉基)，R.sub.4为氢、低烷基、芳基低烷基、二芳基低烷基、芳基或杂环芳基，(c) m为1或2；(d) 每个Z独立地为H、低烷基、卤素、硝基、--NH.sub.2、低烷基羰基氨基、芳基羰基氨基、低烷氧羰基氨基或低烷基氨基；(e) R.sub.1为H、低烷基、芳基低烷基、杂环芳基低烷基、环烷基甲基或低烯基甲基，但当X为O、m为1、Z为H且R.sub.1为甲基时，R不为--CONHCH.sub.3、--CONHC.sub.6H.sub.5、氢、甲基或乙基；当X为O、m为1且Z和R.sub.1都为氢时，R不为氢或甲基。它们的药物可接受的酸盐可用作记忆增强和镇痛剂。
• Memory enhancing and analgesic 1,2,3,3a,8,8a,-hexahydro-3a,8(and
  申请人：Hoechst-Marion-Roussel, Inc.

  公开号：US05639892A1

  公开（公告）日：1997-06-17

  There are described compounds of the formula ##STR1## where X is O or S; (b) R is H, loweralkyl, ##STR2## where Y is O or S; R.sub.2 is alkyl, cycloalkyl, bicyclcalkyl, cycloalkenyl, aryl, arylloweralkyl, heteroaryl or heteroarylloweralkyl, R.sub.3 is H or alkyl, or the group --NR.sub.2.sub.R.sub.3 taken as a whole is 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl or 2-(2,6-dichlorophenylimino)-1-imidazolidinyl) and R.sub.4 is hydrogen, loweralkyl, arylloweralkyl, diarylloweralkyl, aryl or heteroaryl, (c) m is 1 or 2; (d) each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino, and (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heheroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, with the proviso that when X is O, m is l, Z is H and R.sub.1 is methyl, R is not --CONHCH.sub.3, --CONHC.sub.6 H.sub.5, hydrogen, methyl or ethyl, and that when X is O, m is l and Z and R.sub.1 are both hydrogen, R is not hydrogen or methyl, and, pharmaceutically acceptable acid addition salts thereof which are useful as memory-enhancing and analgesic agents.

  描述了一种化合物的公式 ##STR1## 其中X为O或S; (b) R为H，低碳基，##STR2## 其中Y为O或S; R.sub.2为烷基，环烷基，双环烷基，环烯基，芳基，芳基低碳基，杂环芳基或杂环芳基低碳基，R.sub.3为H或烷基，或整个--NR.sub.2.sub.R.sub.3基团为1-吡咯烷基，1-哌啶基，4-吗啉基，4-硫代吗啉基，1-哌嗪基，4-甲基-1-哌嗪基或2-(2,6-二氯苯基亚胺)-1-咪唑烷基)，R.sub.4为氢，低碳基，芳基低碳基，二芳基低碳基，芳基或杂环芳基，(c) m为1或2; (d) 每个Z独立地为H，低碳基，卤素，硝基，--NH.sub.2，低碳基羰基氨基，芳基羰基氨基，低碳基氧羰基氨基或低碳基氨基，和 (e) R.sub.1为H，低碳基，芳基低碳基，杂环芳基低碳基，环烷基甲基或低碳烯基甲基，但须注意当X为O时，m为1，Z为H且R.sub.1为甲基时，R不是--CONHCH.sub.3，--CONHC.sub.6 H.sub.5，氢，甲基或乙基，当X为O，m为1且Z和R.sub.1都为氢时，R不是氢或甲基，以及其药学上可接受的酸盐，其可用作增强记忆和镇痛剂。
• Memory enhancing and analgesic 1,2,3,3a,8,8a-Hexahydro-3a,8(and
  申请人：Hoechst Marion Roussel, Inc.

  公开号：US05663190A1

  公开（公告）日：1997-09-02

  There are described compounds of the formula ##STR1## where (a) X is O or S; (b) R is H, loweralkyl, ##STR2## where Y is O or S; R.sub.2 is alkyl, cycloalkyl, bicycloalkyl, cycloalkenyl, aryl, arylloweralkyl, heteroaryl or heteroarylloweralkyl, R.sub.3 is H or alkyl, or the group --NR.sub.2 R.sub.3 taken as a whole is 1-pyrrolidinyl, 1-piperldinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl or 2-(2,6-dichlorophenylimino)-1-imidazolidinyl) and R.sub.4 is hydrogen, loweralkyl, arylloweralkyl, diarylloweralkyl, aryl or heteroaryl, (c) m is 1 or 2; (d) each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino, and (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heteroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, with the proviso that when X is O, m is 1, Z is H and R.sub.1 is methyl, R is not --CONHCH.sub.3, --CONHC.sub.6 H.sub.5, hydrogen, methyl or ethyl and that when X is O, m is 1 and Z and R.sub.1 are both hydrogen, R is not hydrogen or methyl, and pharmaceutically acceptable acid addition salts thereof which are useful as memory-enhancing and analgesic agents.

  描述了一种化合物的公式##STR1##其中(a) X为O或S; (b) R为H，loweralkyl，##STR2##其中Y为O或S; R.sub.2为烷基，环烷基，双环烷基，环烯基，芳基，芳基loweralkyl，杂环芳基或杂环芳基loweralkyl，R.sub.3为H或烷基，或将--NR.sub.2 R.sub.3群体视为1-吡咯烷基，1-哌啶基，4-吗啉基，4-硫代吗啉基，1-哌嗪基，4-甲基-1-哌嗪基或2-(2,6-二氯苯基亚氨基)-1-咪唑啉基，R.sub.4为氢，loweralkyl，芳基loweralkyl，二芳基loweralkyl，芳基或杂环芳基，(c) m为1或2; (d) 每个Z独立地为H，loweralkyl，卤素，硝基，--NH.sub.2，loweralkylcarbonylamino，arylcarbonylamino，loweralkoxycarbonylamino或loweralkylamino，(e) R.sub.1为H，loweralkyl，芳基loweralkyl，杂环芳基loweralkyl，环烷基甲基或loweralkenylmethyl，但是当X为O，m为1，Z为H且R.sub.1为甲基时，R不是--CONHCH.sub.3，--CONHC.sub.6 H.sub.5，氢，甲基或乙基，当X为O，m为1且Z和R.sub.1均为氢时，R不是氢或甲基，以及其药学上可接受的酸盐，可用作增强记忆和镇痛剂。
• Method of preparing 1,2,3,3a,8,8a-hexahydro-3a,8(and 1,3a,8)-Di(and
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US05541340A1

  公开（公告）日：1996-07-30

  There are described compounds of the formula ##STR1## where (a) X is O or S; (b) R is H, loweralkyl, ##STR2## where Y is O or S; R.sub.2 is alkyl, cycloalkyl, bicycloalkyl, cycloalkenyl, aryl, arylloweralkyl, heteroaryl or heteroarylloweralkyl, R.sub.3 is H or alkyl, or the group --NR.sub.2 R.sub.3 taken as a whole is 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl or 2-(2,6-dichlorophenylimino)-1-imidazolidinyl) and R.sub.4 is hydrogen, loweralkyl, arylloweralkyl, diarylloweralkyl, aryl or heteroaryl, (c) m is 1 or 2; (d) each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino, and (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heteroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, with the proviso that when X is O, m is 1, Z is H and R.sub.1 is methyl, R is not --CONHCH.sub.3, --CONHC.sub.6 H.sub.5, hydrogen, methyl or ethyl, and that when X is O, m is 1 and Z and R.sub.1 are both hydrogen, R is not hydrogen or methyl, and pharmaceutically acceptable acid addition salts thereof which are useful as memory-enhancing and analgesic agents.

  该文描述了式子##STR1##的化合物，其中(a)X为O或S；(b)R为H、loweralkyl、##STR2##其中Y为O或S；R.sub.2为alkyl、cycloalkyl、bicycloalkyl、cycloalkenyl、aryl、arylloweralkyl、heteroaryl或heteroarylloweralkyl，R.sub.3为H或alkyl，或者--NR.sub.2 R.sub.3整体为1-吡咯烷基、1-哌啶基、4-吗啉基、4-硫代吗啉基、1-哌嗪基、4-甲基-1-哌嗪基或2-(2,6-二氯苯基亚胺)-1-咪唑啉基，R.sub.4为氢、loweralkyl、arylloweralkyl、diarylloweralkyl、aryl或heteroaryl，(c)m为1或2；(d)每个Z独立地为H、loweralkyl、卤素、硝基、--NH.sub.2、loweralkylcarbonylamino、arylcarbonylamino、loweralkoxycarbonylamino或loweralkylamino；(e)R.sub.1为H、loweralkyl、arylloweralkyl、heteroarylloweralkyl、cycloalkylmethyl或loweralkenylmethyl，但当X为O、m为1、Z为H且R.sub.1为甲基时，R不为--CONHCH.sub.3、--CONHC.sub.6 H.sub.5、氢、甲基或乙基，当X为O、m为1且Z和R.sub.1均为氢时，R不为氢或甲基，以及其药学上可接受的酸加成盐，其作为增强记忆和镇痛剂。
• Memory enhancing and analgsic 1,2,3,3A,8,8A-Hexahydro--3A,
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US05541216A1

  公开（公告）日：1996-07-30

  There are described compounds of the formula ##STR1## where (a) X is O or S; (b) R is H, loweralkyl, ##STR2## where Y is O or S; R.sub.2 is alkyl, cycloalkyl, bicycloalkyl, cycloalkenyl, aryl, arylloweralkyl, heteroaryl or heteroarylloweralkyl, R.sub.3 is H or alkyl, or the group --NR.sub.2 R.sub.3 taken as a whole is 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl or 2-(2,6-dichlorophenylimino)-1-imidazolidinyl) and R.sub.4 is hydrogen, loweralkyl, arylloweralkyl, diarylloweralkyl, aryl or heteroaryl, (c) m is 1 or 2; each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino, and (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heteroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, with the proviso that when X is O, m is 1, Z is H and R.sub.1 is methyl, R is not --CONHCH.sub.3, --CONHC.sub.6 H.sub.5, hydrogen, methyl or ethyl, and that when X is O, m is 1 and Z and R.sub.1 are both hydrogen, R is not hydrogen or methyl, and pharmaceutically acceptable acid addition salts thereof which are useful as memory-enhancing and analgesic agents.

  描述了一种化合物，其化学式为##STR1##其中：（a）X为O或S；（b）R为H，低碳基，##STR2##其中Y为O或S；R.sub.2为烷基，环烷基，双环烷基，环烯基，芳基，芳基低碳基，杂环芳基或杂环芳基低碳基，R.sub.3为H或烷基，或--NR.sub.2 R.sub.3作为整体为1-吡咯基，1-哌啶基，4-吗啉基，4-硫代吗啉基，1-哌嗪基，4-甲基-1-哌嗪基或2-(2,6-二氯苯基亚胺)-1-咪唑啉基，R.sub.4为氢，低碳基，芳基低碳基，二芳基低碳基，芳基或杂环芳基，（c）m为1或2；每个Z独立地为H，低碳基，卤素，硝基，--NH.sub.2，低碳基羰基氨基，芳基羰基氨基，低碳基氧羰基氨基或低碳基氨基，（e）R.sub.1为H，低碳基，芳基低碳基，杂环芳基低碳基，环烷甲基或低碳烯基甲基，但当X为O，m为1，Z为H且R.sub.1为甲基时，R不是--CONHCH.sub.3，--CONHC.sub.6 H.sub.5，氢，甲基或乙基；当X为O，m为1且Z和R.sub.1均为氢时，R不是氢或甲基。这些化合物的药物可接受酸盐具有增强记忆和镇痛作用。