iodo-beta CCE | 78539-65-8

• 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: iodo-beta CCE
• 英文别名: 6-iodo-β-carbolin-3-carboxylic acid ethyl ester；ethyl 6-iodo-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 78539-65-8
• 化学式: C₁₄H₁₁IN₂O₂
• 分子量: 366.158
• InChiKey: LTYUPBZLKIUGQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  iodo-beta CCE 、 亚磷酸二乙酯 生成 6-Diethoxyphosphoryl-beta-carboline-3-carboxylic-acid-ethylester
  参考文献：
  名称：

  HUTH, A.;SCHMIECHEN, R.;SEIDELMANN, D.;RAHTZ, D.;EDER, U.;NEEF, G.;KEHR, +

  摘要：

  DOI：
• 作为产物：
  描述：

  β-咔啉-3-羧酸乙酯 在 硫酸 、 水 、 碘 、 碘酸 、 溶剂黄146 作用下， 反应 3.0h， 以64%的产率得到iodo-beta CCE
  参考文献：
  名称：

  在苯甲醇中羰基化。一种制备芳族苄基酯的简便新方法

  摘要：

  碘化物2a-c和12a-b在苄醇中用一氧化碳进行羰基化，得到相应的苄基酯3a-c和13a-b，收率很高。结果表明，通过催化氢化可以容易地和选择性地将3a裂解成酸4a。酸转化为酯7a和酰胺6a。

  DOI：

  10.1016/s0040-4020(01)90043-2

文献信息

• .beta.-Carbolin-3-carboxylic acid derivatives
  申请人：A/S Ferrosan

  公开号：US04371536A1

  公开（公告）日：1983-02-01

  A .beta.-carbolin-3-carboxylic acid derivative of the formula ##STR1## has valuable pharmacological properties when administered to patients, e.g. humans as a drug, have been shown to possess interesting tranquilizing activity.

  当给予患者，例如人类作为药物时，具有有价值的药理特性的一种公式为##STR1##的β-咔啉-3-羧酸衍生物已被证明具有有趣的镇静活性。
• Design, synthesis, and subtype selectivity of 3,6-disubstituted β-carbolines at Bz/GABA(A)ergic receptors. SAR and studies directed toward agents for treatment of alcohol abuse
  作者：Wenyuan Yin、Samarpan Majumder、Terry Clayton、Steven Petrou、Michael L. VanLinn、Ojas A. Namjoshi、Chunrong Ma、Brett A. Cromer、Bryan L. Roth、Donna M. Platt、James M. Cook

  DOI：10.1016/j.bmc.2010.08.049

  日期：2010.11

  substituents located at position-3 of the β-carboline nucleus exhibited a conserved stereo interaction in lipophilic pocket L1, while N(2) presumably underwent a hydrogen bonding interaction with H1. Three novel β-carboline ligands (βCCt, 3PBC and WYS8), which preferentially bound to α1 BzR subtypes permitted a comparison of the pharmacological efficacies with a range of classical BzR antagonists (flumazenil

  合成了一系列 3,6-二取代的 β-咔啉，并通过放射性配体结合测定评估了它们对 α x β 3 γ 2 GABA A /苯二氮卓受体亚型的体外亲和力，以寻找治疗酒精滥用的α 1亚型选择性配体。通过 CDI 介导的过程合成了β-咔啉-3-羧酸酯-叔丁酯 (βCCt, 1 ) 的类似物，并通过CDI 介导的过程合成了相关的 6-取代 β-咔啉-3-羧酸酯6包括 WYS8 ( 7 ) Sonogashira 或 Stille 的 6-iodo-βCCt 偶联过程 ( 5 )。βCCt 的二价配体（32和33）也是通过钯催化的自偶联过程设计和制备的，以将构效关系（SAR）扩展到更大的配体。基于药效团/受体模型，对 34 种类似物进行的初步 SAR 研究表明，β-咔啉 6 位的大取代基具有良好的耐受性。正如所预期的，这些基团被提议投射到GABA A /Bz受体的胞外结构域（L Di区域）中（参见32
• Pharmacologically active 3-substituted beta-carbolines
  申请人：Schering Aktiengesellschaft

  公开号：US04435403A1

  公开（公告）日：1984-03-06

  3-substituted beta-carbolines of the formula ##STR1## wherein R.sup.C is hydrogen, lower alkyl, alkoxyalkyl of up to 6 C-atoms, cycloalkyl of 3-6 C-atoms, aralkyl of up to 8 C-atoms, or (CH.sub.2).sub.n OR.sup.20 wherein R.sup.20 is alkyl of up to 6 C-atoms, cycloalkyl of 3-6 C-atoms or aralkyl of up to 8 C-atoms and n is an integer of 1 to 3; Y is oxygen, two hydrogen atoms or NOR.sup.1, wherein R.sup.1 is hydrogen, lower alkyl, aryl or aralkyl of up to 6 C-atoms, COR.sup.2, wherein R.sup.2 is lower alkyl of up to 6 C-atoms, or Y is CHCOOR.sup.3, wherein R.sup.3 is hydrogen or lower alkyl or Y is NNR.sup.4 R.sup.5, wherein R.sup.4 and R.sup.5 can be the same or different and each is hydrogen, lower alkyl, C.sub.6-10 -aryl, C.sub.7-10 -aralkyl or CONR.sup.6 R.sup.7, wherein R.sup.6 and R.sup.7 can be the same or different and each is hydrogen or lower alkyl or R.sup.4 and R.sup.5 together with the connecting N-atom, for a 5- or 6-membered heterocyclic ring which optionally may also contain an O-atom or up to 3 N-atoms and which optionally may be substituted by a lower alkyl group; Z is hydrogen, or alkoxy or aralkoxy each of up to 10 C-atoms and each optionally substituted by hydroxy, or Z is alkyl of up to 6 C-atoms, C.sub.6-10 -aryl or C.sub.7-10 -aralkyl each of which may optionally be substituted by a COOR.sup.8 -- or a CONR.sup.9 R.sup.10 group, wherein R.sup.8 is alkyl of up to 6 C-atoms, and R.sup.9 and R.sup.10 can be the same or different and each is hydrogen or alkyl of up to 6 C-atoms; or Z is NR.sup.9 R.sup.10, wherein R.sup.9 and R.sup.10 are as defined above; or Z is NR.sup.11 CHR.sup.12 R.sup.13, wherein R.sup.11 and R.sup.12 each is hydrogen or together form a N.dbd.C double bond, wherein R.sup.13 is C.sub.1-10 -alkyl or NR.sup.14 R.sup.15, wherein R.sup.14 and R.sup.15 are the same or different and each is hydrogen, OH or alkyl or alkoxy each of up to 6 C-atoms, or wherein R.sup.12 and R.sup.13 together are oxygen, in which case, R.sup.11 is hydrogen; or Z is COOR.sup.2 wherein R.sup.2 is as defined above; or Y and Z, together with the connecting C-atom, may form a 5- or 6-membered heterocyclic ring which contains an O-atom, adjoining O- and N-atoms or up to 4 N atoms and which optionally may be substituted by a lower alkyl group, hydroxy or oxo have valuable psychotropic properties which make them useful for example as tranquilizers.

  该文描述的是一类化合物，即公式为##STR1##的3-取代β-咔啉，其中R.sup.C为氢、低碳基、长达6个碳原子的烷氧基、3-6个碳原子的环烷基、长达8个碳原子的芳基烷基或（CH.sub.2).sub.n OR.sup.20，其中R.sup.20为长达6个碳原子的烷基、3-6个碳原子的环烷基或长达8个碳原子的芳基烷基，n为1至3的整数；Y为氧、两个氢原子或NOR.sup.1，其中R.sup.1为氢、低碳基、长达6个碳原子的芳基或长达8个碳原子的芳基烷基、COR.sup.2，其中R.sup.2为长达6个碳原子的烷基，或Y为CHCOOR.sup.3，其中R.sup.3为氢或低碳基，或Y为NNR.sup.4R.sup.5，其中R.sup.4和R.sup.5可以相同也可以不同，每个都是氢、低碳基、C.sub.6-10-芳基、C.sub.7-10-芳基烷基或CONR.sup.6R.sup.7，其中R.sup.6和R.sup.7可以相同也可以不同，每个都是氢或低碳基，或R.sup.4和R.sup.5与连接的N原子一起形成一个5-或6-成员的杂环环，该环可以含有一个O原子或多达3个N原子，且可以选择性地被低碳基替换；Z为氢，或长达10个碳原子的烷氧基或芳基烷氧基，每个都可以选择性地被羟基取代，或Z为长达6个碳原子的烷基、C.sub.6-10-芳基或C.sub.7-10-芳基烷基，每个都可以选择性地被COOR.sup.8-或CONR.sup.9R.sup.10-基团取代，其中R.sup.8为长达6个碳原子的烷基，R.sup.9和R.sup.10可以相同也可以不同，每个都是氢或长达6个碳原子的烷基；或Z为NR.sup.9R.sup.10，其中R.sup.9和R.sup.10如上所定义；或Z为NR.sup.11CHR.sup.12R.sup.13，其中R.sup.11和R.sup.12每个都是氢或一起形成N.dbd.C双键，其中R.sup.13为C.sub.1-10-烷基或NR.sup.14R.sup.15，其中R.sup.14和R.sup.15可以相同也可以不同，每个都是氢、OH或长达6个碳原子的烷基或烷氧基，或者R.sup.12和R.sup.13一起是氧，此时R.sup.11为氢；或者Z为COOR.sup.2，其中R.sup.2如上所定义；或者Y和Z与连接的C原子一起可以形成一个含有一个O原子、相邻的O和N原子或多达4个N原子的5-或6-成员的杂环环，该环可以选择性地被低碳基、羟基或氧基取代。这些化合物具有有价值的精神药理特性，例如可以用作镇静剂。
• .beta.-carbolin-3-carboxylic acid derivatives useful for treating
  申请人：A/S Ferrosan

  公开号：US05010077A1

  公开（公告）日：1991-04-23

  A .beta.-carbolin-3-carboxylic acid derivative of the formula ##STR1## wherein: X is oxygen, sulphur or NR.sup.10, wherein R.sup.10 is hydrogen, C.sub.1-6 -alkyl, C.sub.1-6 -alkenyl, C.sub.3-7 -cycloalkyl or C.sub.3-7 -cycloalkenyl; R.sup.3 is (a) C.sub.1-10 -alkoxy, C.sub.1-10 -alkenyloxy, C.sub.6-10 -aryloxy, C.sub.7-11 -aralkoxy or C.sub.8-12 -aralkenyloxy, each optionally substituted with one or more hydroxy groups, halogen atoms, CF.sub.3 groups, C.sub.1-10 -alkoxy groups or C.sub.2-4 -alkenyloxy groups or each optionally substituted with an amino, di-C.sub.1-6 -alkylamino, C.sub.1-10 -alkoxycarbonyl or C.sub.1-10 -alkenyloxycarbonyl group; or (b) NR.sup.11 R.sup.12, wherein R.sup.11 and R.sup.12 are the same or different and each is (i) hydrogen, (ii) hydroxy, (iii) C.sub.1-10 -alkyl, (iv) C.sub.2-10 -alkenyl, (v) C.sub.6-10 -aryl, (vi) C.sub.7-11 -aralkyl, (vii) C.sub.8-12 -aralkenyl, (viii) C.sub.3-7 -cycloalkyl, or (ix) C.sub.3-7 -cycloalkenyl, each of groups (iii)-(ix) optionally substituted with hydroxy, carboxamido, carboxy, C.sub.1-10 -alkoxycarbonyl or C.sub.1-10 -alkenyloxycarbonyl; or (x) amino optionally substituted with C.sub.1-10 -alkyl, C.sub.2-10 -alkenyl, C.sub.6-10 -aryl, C.sub.7-11 -aralkyl, C.sub.8-12 -aralkenyl, C.sub.3-7 -cycloalkyl or C.sub.3-7 -cycloalkenyl; or wherein R.sup.11 and R.sup.12 together with the connecting nitrogen atom form a 5-, 6- or 7-membered heterocyclic ring, which may also contain one additional N or one O atom, and which may be optionally substituted with the same groups of substituents listed for groups (iii)-(ix) above, with the proviso that R.sup.11 and R.sup.12 cannot both be hydroxy; or wherein X and R.sup.3 together represent a single nitrogen atom; R.sup.4 is hydrogen, C.sub.1-10 -alkyl, C.sub.2-10 -alkenyl, C.sub.3-7 -cycloalkyl, C.sub.3-7 -cycloalkenyl, C.sub.7-10 -aralkyl, C.sub.8-10 -aralkenyl, phenyl, C.sub.7-10 -alkoxyphenyl or C.sub.8-10 -alkenyloxyphenyl; R.sup.A is F, Cl, Br, I, NO.sub.2, NR.sup.13 R.sup.14, NHCOR.sup.13, CN, COOR.sup.13, OR.sup.13, SCH.sub.3 or SO.sub.2 NR.sup.11 R.sup.12, wherein R.sup.13 and R.sup.14 each is hydrogen or C.sub.1-6 -alkyl optionally substituted with hydroxy or halogen; and wherein R.sup.11 and R.sup.12 are as defined above, and wherein there may be 1-4 identical or different R.sup.A 's; and R.sup.9 is hydrogen, C.sub.1-8 -alkyl, C.sub.1-8 -alkenyl, C.sub.1-8 -alkoxycarbonyl, C.sub.1-8 -alkenyloxycarbonyl, or C.sub.1-8 -alkenyloxy; with the proviso that R.sup.11 and R.sup.12 are not both hydrogen, when X is oxygen and when R.sup.4, R.sup.A and R.sup.9 each is hydrogen; that one of R.sup.11 and R.sup.12 is not hydrogen when the other is amino and when X is oxygen and R.sup.4, R.sup.A and R.sup.9 each are hydrogen; and that R.sup.4, R.sup.A and R.sup.9 each is not hydrogen when X is oxygen and R.sup.3 is OCH.sub.3. have valuable pharmacological properties.

  具有以下结构的.beta.-carbolin-3-羧酸衍生物：##STR1## 其中：X为氧、硫或NR.sup.10，其中R.sup.10为氢、C.sub.1-6-烷基、C.sub.1-6-烯基、C.sub.3-7-环烷基或C.sub.3-7-环烯基；R.sup.3为(a) C.sub.1-10-烷氧基、C.sub.1-10-烯氧基、C.sub.6-10-芳氧基、C.sub.7-11-芳基烷氧基或C.sub.8-12-芳基烯氧基，每个基团可选地取代为一个或多个羟基、卤原子、CF.sub.3基团、C.sub.1-10-烷氧基或C.sub.2-4-烯氧基，或每个基团可选地取代为氨基、双C.sub.1-6-烷基氨基、C.sub.1-10-烷氧羰基或C.sub.1-10-烯氧羰基基团；或(b) NR.sup.11R.sup.12，其中R.sup.11和R.sup.12相同或不同，且每个基团为(i)氢、(ii)羟基、(iii)C.sub.1-10-烷基、(iv)C.sub.2-10-烯基、(v)C.sub.6-10-芳基、(vi)C.sub.7-11-芳基烷基、(vii)C.sub.8-12-芳基烯基、(viii)C.sub.3-7-环烷基或(ix)C.sub.3-7-环烯基，每个基团(iii)-(ix)可选地取代为羟基、羧酰胺基、羧酸基、C.sub.1-10-烷氧羰基或C.sub.1-10-烯氧羰基；或(x)氨基，可选地取代为C.sub.1-10-烷基、C.sub.2-10-烯基、C.sub.6-10-芳基、C.sub.7-11-芳基烷基、C.sub.8-12-芳基烯基、C.sub.3-7-环烷基或C.sub.3-7-环烯基；或其中R.sup.11和R.sup.12与连接氮原子形成5、6或7成员杂环环，该环还可以包含一个额外的N或一个O原子，该环也可以选择地用上述(iii)-(ix)组的取代基团替换，但R.sup.11和R.sup.12不能同时为羟基；或其中X和R.sup.3共同表示单个氮原子；R.sup.4为氢、C.sub.1-10-烷基、C.sub.2-10-烯基、C.sub.3-7-环烷基、C.sub.3-7-环烯基、C.sub.7-10-芳基烷基、C.sub.8-10-芳基烯基、苯基、C.sub.7-10-烷氧基苯基或C.sub.8-10-烯氧基苯基；R.sup.A为F、Cl、Br、I、NO.sub.2、NR.sup.13R.sup.14、NHCOR.sup.13、CN、COOR.sup.13、OR.sup.13、SCH.sub.3或SO.sub.2NR.sup.11R.sup.12，其中R.sup.13和R.sup.14各自为氢或C.sub.1-6-烷基，可选地取代为羟基或卤原子；其中R.sup.11和R.sup.12如上所定义，且可能有1-4个相同或不同的R.sup.A；R.sup.9为氢、C.sub.1-8-烷基、C.sub.1-8-烯基、C.sub.1-8-烷氧羰基、C.sub.1-8-烯氧羰基或C.sub.1-8-烯氧基；但有以下规定：当X为氧，且R.sup.4、R.sup.A和R.sup.9均为氢时，R.sup.11和R.sup.12不能同时为氢；当X为氧，且R.sup.4、R.sup.A和R.sup.9均为氢时，当另一个为氨基时，R.sup.11和R.sup.12中的一个不能为氢；当X为氧且R.sup.3为OCH.sub.3时，R.sup.4、R.sup.A和R.sup.9中的每一个都不能为氢。具有有价值的药理学性质。
• Beta-carbolin-3-carboxylic acid derivatives, pharmaceutical compositions containing them and their therapeutical use
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0030254A1

  公开（公告）日：1981-06-17

  β-Carbolin-3-carboxylic acid derivatives of the formula wherein X, R3, R4, R9 and RA have various significances. These compounds possess valuable pharmacological properties. In particular, they act on the central nervous system and are suitable for use in psychopharmaceutical preparations.

  式中β-咔啉-3-羧酸衍生物 其中 X、R3、R4、R9 和 RA 具有不同的含义。 这些化合物具有宝贵的药理特性。特别是，它们可作用于中枢神经系统，适用于精神药物制剂。