methyl 1-(4-hydroxy-3-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate | 528524-55-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: methyl 1-(4-hydroxy-3-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate
• 英文别名: cis-1-(3-methoxy-4-hydroxyphenyl)-3-carbomethoxy-1,2,3,4,tetrahydro-β-carboline；Methyl 1,2,3,4-Tetrahydro-l-(4-Hydroxy-3-Methoxyphenyl)-9H-Pyrido(3,4-b)Indole-3-Carboxylate；methyl 1-(4-hydroxy-3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 528524-55-2
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: BGCTZYDFAWJFDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-色氨酸甲酯 、 香草醛 以gave the title compound as a cream solid m.p.: 195° C.的产率得到methyl 1-(4-hydroxy-3-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate
  参考文献：
  名称：

  Tetracyclic derivatives, process of preparation and use

  摘要：

  化合物公式(I) ##STR1## 以及其盐和溶剂化物，其中：R.sup.0代表氢、卤素或C.sub.1-6烷基；R.sup.1代表氢、C.sub.1-6烷基、C.sub.2-6烯基、C.sub.2-6炔基、卤代C.sub.1-6烷基、C.sub.3-8环烷基、C.sub.3-8环烷基C.sub.1-3烷基、芳基C.sub.1-3烷基或杂环芳基C.sub.1-3烷基；R.sup.2代表一个可选的取代的单环芳香环，选择自苯、噻吩、呋喃和吡啶或一个可选的取代的双环环 ##STR2## 通过苯环碳原子之一连接到分子的其余部分，其中融合环A是一个5-或6-成员环，可以是饱和的或部分或完全不饱和的，并包括碳原子和可选的一个或两个来自氧、硫和氮的杂原子；R.sup.3代表氢或C.sub.1-3烷基，或R.sup.1和R.sup.3一起代表一个3-或4-成员的烷基或烯基链。公式(I)化合物是环鸟苷酸3'，5'-单磷酸特异性磷酸二酯酶（CGMP特异性PDE）的有效选择性抑制剂，在许多治疗领域中具有有益的抑制作用，包括心血管疾病的治疗。

  公开号：

  US06025494A1

文献信息

• Cytotoxic and Insecticidal Activities of Derivatives of Harmine, a Natural Insecticidal Component Isolated from Peganum harmala
  作者：Yong Zeng、Yaomou Zhang、Qunfang Weng、Meiying Hu、Guohua Zhong

  DOI：10.3390/molecules15117775

  日期：——

  develop novel β-carbolines endowed with better insecticidal activity, a simple high-yielding method for the synthesis of harmine compounds starting from L-tryptophan has been developed and a series of 1,3-substituted β-carboline derivatives have been synthesized and evaluated for their cytotoxicity against insect cultured Sf9 cell line in vitro and insecticidal activities against 4th instar larvae of mosquitos

  在不断努力开发具有更好杀虫活性的新型 β-咔啉的过程中，开发了一种以 L-色氨酸为原料合成有害化合物的简单高产方法，并开发了一系列 1,3-取代的 β-咔啉衍生物合成并评估了它们对昆虫培养的 Sf9 细胞系的体外细胞毒性和对蚊子 4 龄幼虫库蚊和芥子蚜虫 Lipaphis erysimi 的杀虫活性。结果表明，1-苯基-1,2,3,4-四氢-β-咔啉-3-羧酸（化合物2）和1-苯基-β-咔啉-3-羧酸甲酯（化合物13）代表最佳潜在的化合物，在 50-200 mg/L 的浓度下处理 24 小时后，Sf9 细胞的抑制率分别为 71.55% 和 60.21%。化合物2和13对蚊子4龄幼虫也表现出较强的杀虫活性，LC(50)值为20.82 mg/L和23.98 mg/L，LC(90)值为88.29 mg/L和295.13 mg/L ， 分别。此外，化合物2和13对芥菜蚜虫的LC(50)值为53.16
• Tetracyclic derivatives, process of preparation and use
  申请人：ICOS Corporation

  公开号：US20020119976A1

  公开（公告）日：2002-08-29

  A compound of formula (I) 1 and salts and solvates thereof, in which: R o represents hydrogen, halogen or C 1-6 alkyl; R 1 represents hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, halo C 1-6 alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl C 1-3 alkyl, arylC 1-3 alkyl or heteroaryl C 1-3 alkyl; R 2 represents an optionally substituted monocyclic aromatic ring selected from benzene, thiophene, furan and pyridine or an optionally substituted bicyclic ring 2 attached to the rest of the molecule via one of the benzene ring carbon atoms and wherein the fused ring A is a 5- or 6-membered ring which may be saturated or partially or fully unsaturated and comprises carbon atoms and optionally one or two heteroatoms selected from oxygen, sulphur and nitrogen; and R 3 represents hydrogen or C 1-3 alkyl, or R 1 and R 3 together represent a 3- or 4-membered alkyl or alkenyl chain. A compound of formula (I) is a potent and'selective inhibitor of cyclic guanosine 3′, 5′-monophosphate specific phosphodiesterase (CGMP specific PDE) having a utility in a variety of therapeutic areas where such inhibition is beneficial, including the treatment of cardiovascular disorders.

  式(I)1的化合物及其盐和溶剂化物，其中：R代表氢，卤素或C1-6烷基；R1代表氢，C1-6烷基，C2-6烯基，C2-6炔基，卤代C1-6烷基，C3-8环烷基，C3-8环烷基C1-3烷基，芳基C1-3烷基或杂环芳基C1-3烷基；R2代表一个可选的取代的单环芳香环，选择自苯，噻吩，呋喃和吡啶或一个可选的取代的二环2，通过苯环碳原子之一连接到分子的其余部分，其中融合的环A是一个5-或6-成员环，可以是饱和的或部分或完全不饱和的，并包括碳原子和可选的一个或两个异原子，选择自氧，硫和氮；R3代表氢或C1-3烷基，或R1和R3一起代表一个3-或4-成员烷基或烯基链。式(I)的化合物是环鸟苷3'，5'-单磷酸特异性磷酸二酯酶（CGMP特异性PDE）的有效和选择性抑制剂，具有在多种治疗领域中抑制有益的功效，包括心血管疾病的治疗。
• Method of inhibiting neoplastic cells with tetracyclic pyrido[3,4-B] indole derivatives
  申请人：——

  公开号：US20020035111A1

  公开（公告）日：2002-03-21

  A method for inhibiting neoplasia, particularly cancerous and precancerous lesions by exposing the affected cells to pyrido[3,4b]indoles.

  一种通过将受影响的细胞暴露于吡啶并［3,4b］吲哚来抑制肿瘤，特别是癌症和癌前病变的方法。
• Tetracyclic derivatives; process of preparation and use
  申请人：ICOS Corporation

  公开号：US05859006A1

  公开（公告）日：1999-01-12

  A compound of formula (I) ##STR1## and salts and solvates thereof, in which: R.sup.0 represents hydrogen, halogen or C.sub.1-6 alkyl; R.sup.1 represents hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, haloC.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkylC.sub.1-3 alkyl, arylC.sub.1-3 alkyl or heteroarylC.sub.1-3 alkyl; R.sup.2 represents an optionally substituted monocyclic aromatic ring selected from benzene, thiophene, furan and pyridine or an optionally substituted bicyclic ring ##STR2## attached to the rest of the molecule via one of the benzene ring carbon atoms and wherein the fused ring A is a 5- or 6-membered ring which may be saturated or partially or fully unsaturated and comprises carbon atoms and optionally one or two heteroatoms selected from oxygen, sulphur and nitrogen; and R.sup.3 represents hydrogen or C.sub.1-3 alkyl, or R.sup.1 and R.sup.3 together represent a 3- or 4-membered alkyl or alkenyl chain. A compound of formula (I) is a potent and selective inhibitor of cyclic guanosine 3', 5'-monophosphate specific phosphodiesterase (cGMP specific PDE) having a utility in a variety of therapeutic areas where such inhibition is beneficial, including the treatment of cardiovascular disorders.

  化合物的公式(I) ##STR1## 及其盐和溶剂化物，其中：R.sup.0代表氢，卤素或C.sub.1-6烷基；R.sup.1代表氢，C.sub.1-6烷基，C.sub.2-6烯基，C.sub.2-6炔基，卤代C.sub.1-6烷基，C.sub.3-8环烷基，C.sub.3-8环烷基C.sub.1-3烷基，芳基C.sub.1-3烷基或杂芳基C.sub.1-3烷基；R.sup.2代表一种可选的取代的单环芳香环，选择自苯，噻吩，呋喃和吡啶或一种可选的取代的双环环 ##STR2## 通过苯环碳原子之一连接到分子的其余部分，并且融合的环A是一个5-或6-成员环，可以是饱和的或部分或完全不饱和的，并且包括碳原子和可选的一个或两个来自氧，硫和氮的杂原子；R.sup.3代表氢或C.sub.1-3烷基，或R.sup.1和R.sup.3一起代表3-或4-成员烷基或烯基链。公式(I)的化合物是环鸟苷3'，5'-单磷酸特异性磷酸二酯酶（cGMP特异性PDE）的有效选择性抑制剂，在许多治疗领域中具有益处，包括心血管疾病的治疗。
• (6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione for the treatment of benign prostatic hypertrophy
  申请人：ICOS Corporation

  公开号：EP2036560A1

  公开（公告）日：2009-03-18

  Compound (6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino [2', 1':6,1]pyrido[3,4-b]indcle-1,4-dione for the treatment of benign prostatic hypertrophy.

  用于治疗良性前列腺肥大的化合物 (6R,12aR)-2,3,6,7,12,12a-六氢-2-甲基-6-(3,4-亚甲基二氧苯基)-吡嗪并[2', 1':6,1]pyrido[3,4-b]indcle-1,4- 二酮。