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
• 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。
• Tetracyclic cyclic gmp-specific phosphodiesterase inhibitors for the treatment of benign prostatic hypertrophy
  申请人：ICOS Corporation

  公开号：EP2327408A1

  公开（公告）日：2011-06-01

  A compound of formula (1) and salts and solvates thereof, in which: R0 represents hydrogen, halogen, or Cl-6alkyl; R1 represents hydrogen, C1-6-alkyl, C2-6alkenyl, C2-6alkynyl, haloC1-6alkyl, C3-8cycloalkyl, C3-8cyloalkylcl-3alkyl, arylC1-3alkyl, or heteroarylcl-3alkyl; R2 represents an optionally substituted monocyclic aromatic ring selected from benzene, thiophene, furan, and pyridine, or an optionally substituted bicyclic ring (a) 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 R3 represents hydrogen or Cl-alkyl, or R1 and R3 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 benign prostatic hypertrophy.

  式(1)化合物及其盐和溶剂，其中：R0 代表氢、卤素或 Cl-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-环烷基环 3 烷基、芳基 C1-3 烷基或杂芳基环 3 烷基；R2 代表任选取代的单环芳香环，选自苯、噻吩、呋喃和吡啶，或任选取代的双环 (a)，通过其中一个苯环碳原子连接到分子的其余部分，其中融合环 (A) 是 5 或 6 元环，可以是饱和环或部分或完全不饱和环，包括碳原子和任选选自氧、硫和氮的一个或两个杂原子；R3 代表氢或 Cl-烷基，或 R1 和 R3 共同代表 3 或 4 元烷基或烯基链。式（I）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）的强效选择性抑制剂，可用于多种治疗领域，包括治疗良性前列腺肥大。