2-benzyl-5-phenyl-1,2,3,4-tetrahydropyrido<4,3b>indole | 6208-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-benzyl-5-phenyl-1,2,3,4-tetrahydropyrido<4,3b>indole
• 英文别名: 2-benzyl-5-phenyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；2-Benzyl-5-phenyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；2-benzyl-5-phenyl-3,4-dihydro-1H-pyrido[4,3-b]indole
• CAS: 6208-47-5
• 化学式: C₂₄H₂₂N₂
• 分子量: 338.452
• InChiKey: BAPCUXNMDQTRAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzyl-5-phenyl-1,2,3,4-tetrahydropyrido<4,3b>indole 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 氨 、 氢气 、 sodium 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0~55.0 ℃ 、379.21 kPa 条件下， 反应 9.0h， 生成 cis-(+/-)-5-(4-fluorophenyl)-2-<4-hydroxy-4-(4-fluorophenyl)butyl>-2,3,4,4a,5,9b-hexahydro-1H-pyrido<4,3b>indole
  参考文献：
  名称：

  Neuroleptics from the 4a,9b-cis- and 4a,9b-trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole series. 2

  摘要：

  Compounds derived from 4a,9b-trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4, 3-b]indole are consistently efficacious in displacing [3H]spiroperidol from striatal dopamine receptors in vitro. Derivatives bearing substituents at position 2, particularly those derived from butyrophenone moieties, are exceptionally potent in vivo. Compounds from the corresponding 4a,9b-cis series are substantially less potent in both in vivo and in vitro assays of neuroleptic activity. Although the cis and trans derivatives have, in some conformations, similar basic nitrogen atom to aromatic ring separations of about 5.1 A, the distance at which the basic nitrogen atom lies above or below the plane of the aromatic ring differs substantially between the two series. Consideration of these results in terms of this and earlier work indicates that the out-of-plane distance for the basic nitrogen in neuroleptic molecules may range from about 0 to about 0.90 A but may be optimized at about 0.55 A.

  DOI：

  10.1021/jm00160a050

文献信息

• 2-Substitute
  申请人：Pfizer Inc.

  公开号：US04224329A1

  公开（公告）日：1980-09-23

  2-Substituted-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles of the formula (I): ##STR1## and the pharmaceutically-acceptable salts thereof, wherein the hydrogen atoms in the 4a position and 9b positions are in a trans relationship to each other and the 5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole moiety is dextrorotatory; X.sub.1 and Y.sub.1 are the same or different and are each hydrogen or fluoro; Z.sub.1 is hydrogen, fluoro or methoxy; M is a member selected from the group consisting of ##STR2## a mixture thereof and C.dbd.O and n is 3 or 4; their use as tranquilizing agents, pharmaceutical compositions containing them and a process for their production.

  式(I)中的2-取代-5-芳基-2,3,4,4a,5,9b-六氢-1H-吡啶[4,3-b]吲哚及其药学上可接受的盐，其中4a位和9b位的氢原子相对构型为反式，5-芳基-2,3,4,4a,5,9b-六氢-1H-吡啶[4,3-b]吲哚基团为右旋性；X1和Y1相同或不同，分别为氢或氟；Z1为氢、氟或甲氧基；M为从以下组中选择的成员：##STR2## 其混合物和C.dbd.O，n为3或4；它们作为镇静剂的用途，包含它们的制药组合物以及它们的制备过程。
• 2-Substituted-trans-5-ar
  申请人：Pfizer Inc.

  公开号：US04252812A1

  公开（公告）日：1981-02-24

  2-Substituted-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles of the formula (I): ##STR1## and the pharmaceutically-acceptable salts thereof, wherein the hydrogen atoms in the 4a position and 9b positions are in a trans relationship to each other and the 5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole moiety is dextrorotatory; X.sub.1 and Y.sub.1 are the same or different and are each hydrogen or fluoro; Z.sub.1 is hydrogen, fluoro or methoxy; M is a member selected from the group consisting of ##STR2## a mixture thereof and C=0 and n is 3 or 4; their use as tranquilizing agents, pharmaceutical compositions containing them and a process for their production.

  式(I)的2-取代-5-芳基-2,3,4,4a,5,9b-六氢-1H-吡啶[4,3-b]吲哚及其药学上可接受的盐，其中4a位和9b位的氢原子相对构型为反式，5-芳基-2,3,4,4a,5,9b-六氢-1H-吡啶[4,3-b]吲哚基团为右旋性；X.sub.1和Y.sub.1相同或不同，分别为氢或氟；Z.sub.1为氢、氟或甲氧基；M为从以下组中选择的成员之一：##STR2## 其混合物和C=0，n为3或4；它们作为镇静剂的用途，包含它们的制药组合物以及它们的制备方法。
• Process for the production of 2-substituted pyrido[4,3-b]-indoles
  申请人：Pfizer Inc.

  公开号：US04267331A1

  公开（公告）日：1981-05-12

  A process for production of certain 2-substituted-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole tranquilizing agents of the formula ##STR1## wherein X.sub.1 and Y.sub.1 are each hydrogen or fluoro; Z.sub.1 is hydrogen, fluoro or methoxy and n is 3 or 4 which comprises contacting an amine of the formula ##STR2## with an equimolar amount of a lactol of the formula ##STR3## wherein q is 1 or 2; in the presence of a reaction inert solvent under reductive alkylation conditions.

  一种生产某些2-取代-5-芳基-2,3,4,4a,5,9b-六氢-1H-吡啶[4,3-b]吲哚镇静剂的工艺，其化学式为##STR1##其中X1和Y1分别为氢或氟；Z1为氢、氟或甲氧基，n为3或4，包括在还原烷基化条件下，在反应惰性溶剂存在下，将式##STR2##的胺与式##STR3##的内酯以当量反应。其中q为1或2。
• 5-(4-Fluorophenyl)tetrahydro-2-furanol
  申请人：Pfizer Inc.

  公开号：US04277404A1

  公开（公告）日：1981-07-07

  2-Substituted-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles of the formula (I): ##STR1## and the pharmaceutically-acceptable salts thereof, wherein the hydrogen atoms in the 4a position and 9b positions are in a trans relationship to each other and the 5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole moiety is dextrorotatory; X.sub.1 and Y.sub.1 are the same or different and are each hydrogen or fluoro; Z.sub.1 is hydrogen, fluoro or methoxy; M is a member selected from the group consisting of ##STR2## a mixture thereof and C.dbd.O and n is 3 or 4; their use as tranquilizing agents, pharmaceutical compositions containing them and a process for their production.

  公式（I）的2-取代-5-芳基-2,3,4,4a,5,9b-六氢-1H-吡啶[4,3-b]吲哚及其药学上可接受的盐，其中4a位和9b位的氢原子相对于彼此处于反式关系，而5-芳基-2,3,4,4a,5,9b-六氢-1H-吡啶[4,3-b]吲哚基团为右旋性；X1和Y1相同或不同，均为氢或氟；Z1为氢、氟或甲氧基；M为从以下组中选择的成员：##STR2## 其混合物和C.dbd.O，n为3或4；其作为镇静剂的用途，包含它们的制药组合物以及它们的制备过程。
• US4224329A
  申请人：——

  公开号：US4224329A

  公开（公告）日：1980-09-23