(1R,3S)-1-(4'-hydroxy-3'-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

• 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: (1R,3S)-1-(4'-hydroxy-3'-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
• 英文别名: (1R,3S)-1-(4-hydroxy-3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid；trans-1-(4’-hydroxy-3’-methoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid；(1R,3S)-1-(4-hydroxy-3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-3-carboxylate
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: FJJFUMBHEOHXLC-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  94.6
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-重氮基氨基甲酸叔-丁基酯 、 (1R,3S)-1-(4'-hydroxy-3'-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 生成 (1R,3S)-1-(4-hydroxy-3-methoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylic acid
  参考文献：
  名称：

  A new class of β-carboline alkaloid-peptide conjugates with therapeutic efficacy in acute limb ischemia/reperfusion injury

  摘要：

  We describe a novel class of beta-carboline alkaloid-peptide conjugates that possess both free radical scavenging and thrombolytic activity. These conjugates demonstrate therapeutic efficacy in a rat arterial thrombosis assay, as well as free radical scavenging capacity as evaluated in a PC12 cell survival assay. Our results indicate that beta-carboline alkaloid-peptide conjugate 26a exerts a significant protective effect against local and remote organ injury induced by limb I/R injury in the rat. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.01.021
• 作为产物：
  描述：

  香草醛 、 L-色氨酸 在 溶剂黄146 作用下， 反应 4.0h， 以12%的产率得到(1R,3S)-1-(4'-hydroxy-3'-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
  参考文献：
  名称：

  肥大细胞稳定剂1-（4-羟基-3-甲氧基苯基）-2,3,4,9-四氢-1H-β-咔啉-3-羧酸衍生物的合成

  摘要：

  肥大细胞的作用可以是保护性的或有害的；取决于它们被激活的生理/病理状况。后者的作用是由于肥大细胞脱粒和一系列燃烧介质的释放。肥大细胞在诸如变态反应，湿疹，过敏性休克，肥大细胞增多症以及其他各种肥大细胞疾病中具有公认的作用。以前，我们已经证明螺-β-咔啉烷基化类似物具有肥大细胞稳定活性。最近，色氨酸被报道抑制肥大细胞的活化。实际上，据报道香兰素类似物抑制脱粒。因此，值得合成21个色氨酸与香草醛的受限类似物，它们是2,3,4,9-四氢-β-咔啉-3-羧酸的衍生物，并对其进行离体评估抑制化合物48/80诱导的肥大脱粒活性。通过将IC 50（µM）值与标准药物克罗莫林钠（IC 50  = 0.486±0.003 µM）进行比较，可得到大体积的基团化合物，如三取代异丙基（化合物7；顺式-1-（4-异丙氧基-3-甲氧基苯基）- 2,9-二异丙基-2,3,4,9-四氢-1 H -β-咔啉-3-羧酸; IC

  DOI：

  10.1007/s00044-020-02555-y

文献信息

• 1H- und13C-NMR-spektroskopische Zuordnung der cis- und trans-Isomere einiger 1-Aryl-1,2,3,4-tetrahydro-β-carbolin-3-carbonsäuren bzw. deren Methylester
  作者：Ulf Pindur

  DOI：10.1002/ardp.19803130414

  日期：——

  An Hand der chemischen Verschiebungen des C‐1‐Protons in den 1H‐NMR‐ und der C‐1 und C‐3‐Kohlenstoffe in den 13C‐NMR‐Spektren werden die durch fraktionierte Kristallisation erhaltenen Isomere von 3 und 4 den cis‐ und trans‐Formen zugeordnet.

  根据 1H NMR 中 C-1 质子的化学位移和 13C NMR 光谱中 C-1 和 C-3 碳的化学位移，通过分级结晶获得的 3 和 4 的异构体是顺式并归为反式。
• <scp>l</scp>-Tryptophan Reacts with Naturally Occurring and Food-Occurring Phenolic Aldehydes To Give Phenolic Tetrahydro-β-carboline Alkaloids:  Activity as Antioxidants and Free Radical Scavengers
  作者：Tomas Herraiz、Juan Galisteo、Cristina Chamorro

  DOI：10.1021/jf0210066

  日期：2003.4.1

  The reaction between the essential amino acid L-tryptophan and flavoring or naturally occurring phenyl and phenolic aldehydes was studied, and the alkaloidal reaction products were characterized by NMR and HPLC-MS. Benzaldehyde, vanillin, syringaldehyde, salicylaldehyde, and anisaldehyde condensed with L-tryptophan in aqueous-acidic media affording the corresponding phenolic tetrahydro-beta-carboline-3-carboxylic acid as two diastereoisomers, 1 S,3S-cis and 1R,3S-trans. With the exception of benzaldehyde, the rest of the aldehydes needed heating conditions (70 degreesC) to significantly form tetrahydro-beta-carbolines over time with the cyclization highly favored at low pH. This suggests a likely formation of these compounds under conditions that may occur in foods, food processing, or cooking. The new phenolic tetralhydro-beta-carboline alkaloids were assayed, for the first time, for their activity as free radical scavengers and antioxidants and showed good antioxidant properties with Trolox equivalent antioxidant capacity (TEAC) values much higher than those of ascorbic acid and the water soluble vitamin E analogue, Trolox, in the 2,2'-azinobis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS) assay.
• Discovery of novel phosphatidylcholine-specific phospholipase C drug-like inhibitors as potential anticancer agents
  作者：Chatchakorn Eurtivong、Lisa I. Pilkington、Michelle van Rensburg、Reuben M. White、Harpreet Kaur Brar、Shaun Rees、Emily K. Paulin、Chris Sun Xu、Nabangshu Sharma、Ivanhoe K.H. Leung、Euphemia Leung、David Barker、Jóhannes Reynisson

  DOI：10.1016/j.ejmech.2019.111919

  日期：2020.2

  Phosphatidylcholine-specific phospholipase C (PC-PLC) is a promising target for new anticancer treatment. Herein, we report our work in the discovery of novel drug-like PC-PLC inhibitors. Virtual screening led to the identification of promising hits from four different structural series that contain the molecular scaffold of benzenesulphonamides (10), pyrido[3,4-b]indoles (22), morpholinobenzoic acid (84) and benzamidobenzoic acid (80). 164 structural analogues were tested to investigate the chemical space around the hit series and to generate preliminary structurally activity relationships (SAR). Two of the pyrido[3,4-b]indoles (22_10 and 22_15) had comparable or better potency as D609, an established but non-drug-like PC-PLC inhibitor. Furthermore, three morpholinobenzoic acids (84, 84_4 and 84_5) had superior potency than D609. Therefore, this study paves the way towards the development of drug-like PL-PLC inhibitors as potential anticancer agents. (C) 2019 Elsevier Masson SAS. All rights reserved.
• A new class of β-carboline alkaloid-peptide conjugates with therapeutic efficacy in acute limb ischemia/reperfusion injury
  作者：Wei Bi、Yue Bi、Ping Xue、Yanrong Zhang、Xiang Gao、Zhibo Wang、Meng Li、Michèle Baudy-Floc’h、Nathaniel Ngerebara、K. Michael Gibson、Lanrong Bi

  DOI：10.1016/j.ejmech.2011.01.021

  日期：2011.5

  We describe a novel class of beta-carboline alkaloid-peptide conjugates that possess both free radical scavenging and thrombolytic activity. These conjugates demonstrate therapeutic efficacy in a rat arterial thrombosis assay, as well as free radical scavenging capacity as evaluated in a PC12 cell survival assay. Our results indicate that beta-carboline alkaloid-peptide conjugate 26a exerts a significant protective effect against local and remote organ injury induced by limb I/R injury in the rat. Published by Elsevier Masson SAS.
• Synthesis of 1-(4-hydroxy-3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid derivatives as mast cell stabilizers
  作者：Karan Saini、Jatinder Singh、Ramanpreet Shah、Jaspreet Kaur、Dhandeep Singh、Nirmal Singh、Amteshwar Singh Jaggi、Dimple Sethi Chopra、Ram Sarup Singh

  DOI：10.1007/s00044-020-02555-y

  日期：2020.8

  9-diisopropyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid; IC50 = 0.389 ± 0.015 µM) and tri-substituted octyl (compound 17; cis-1-(3’-Methoxy-4’-(octyloxy)phenyl)-2,9-dioctyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid; IC50 = 0.237 ± 0.031 µM) were found to be equipotent. Furthermore, the polar group SO2 containing compound tosyl derivative (compound 21; cis-1-(4’-hydroxy-3’-methoxyphenyl)-2-tosyl-2

  肥大细胞的作用可以是保护性的或有害的；取决于它们被激活的生理/病理状况。后者的作用是由于肥大细胞脱粒和一系列燃烧介质的释放。肥大细胞在诸如变态反应，湿疹，过敏性休克，肥大细胞增多症以及其他各种肥大细胞疾病中具有公认的作用。以前，我们已经证明螺-β-咔啉烷基化类似物具有肥大细胞稳定活性。最近，色氨酸被报道抑制肥大细胞的活化。实际上，据报道香兰素类似物抑制脱粒。因此，值得合成21个色氨酸与香草醛的受限类似物，它们是2,3,4,9-四氢-β-咔啉-3-羧酸的衍生物，并对其进行离体评估抑制化合物48/80诱导的肥大脱粒活性。通过将IC 50（µM）值与标准药物克罗莫林钠（IC 50  = 0.486±0.003 µM）进行比较，可得到大体积的基团化合物，如三取代异丙基（化合物7；顺式-1-（4-异丙氧基-3-甲氧基苯基）- 2,9-二异丙基-2,3,4,9-四氢-1 H -β-咔啉-3-羧酸; IC