(1R,3S)-1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid | 182074-37-9

• 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-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
• 英文别名: (1R,3S)-2,3,4,9-tetrahydro-1-phenyl-1H-pyrido[3,4-b]indole-3-carboxylic acid；(1R,3S)-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid；(1R,3S)-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-3-carboxylate
• CAS: 182074-37-9
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: ZJSUEWDIHUPPRO-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氨甲基苯甲酸甲酯 、 (1R,3S)-1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Re-exploration of tetrahydro-β-carboline scaffold: Discovery of selective histone deacetylase 6 inhibitors with neurite outgrowth-promoting and neuroprotective activities

  摘要：

  DOI：

  10.1016/j.bmcl.2024.129670
• 作为产物：
  描述：

  methyl (1R,3S)-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 在 amberlyst hydroxide 作用下， 生成 (1R,3S)-1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
  参考文献：
  名称：

  靶向2 - C-甲基-d-赤藓糖醇4-磷酸胞苷基转移酶（IspD）的抗疟剂（1 R，3 S）-MMV008138的生物学研究和目标参与

  摘要：

  疟疾仍然是世界上最致命的疾病之一，耐药性寄生虫的出现一直是威胁。疟原虫寄生虫利用甲基赤藓糖醇磷酸酯（MEP）途径来合成异戊烯基焦磷酸酯（IPP）和二甲基烯丙基焦磷酸酯（DMAPP），这对于寄生虫的生长至关重要。以前，我们和其他人发现，疟疾框化合物MMV008138靶向于原生质体，并且该化合物对寄生虫的生长抑制作用可以通过补充IPP来逆转。进一步的工作表明，MMV008138靶向2- C-甲基-d酶。MEP途径中的-赤藓糖醇4-磷酸胞苷转移酶（IspD），可将MEP和胞苷三磷酸（CTP）转化为胞苷二磷酸甲基赤藓糖醇（CDP-ME）和焦磷酸。在这项工作中，我们试图通过探索MMV008138类似物抑制Pf IspD重组酶的能力来深入了解结构与活性之间的关系。这里，我们报告Pf的ISPD抑制数据用于膦胺霉素（FOS）和19个以前公开的类似物和报告寄生虫生长和Pf的ISPD抑制数据用于MMV0081

  DOI：

  10.1021/acsinfecdis.7b00159

文献信息

• Microwave accelerated Pictet–Spengler reactions of tryptophan with ketones directed toward the preparation of 1,1-disubstituted indole alkaloids
  作者：Fu-Ming Kuo、Ming-Chung Tseng、Ya-Hew Yen、Yen-Ho Chu

  DOI：10.1016/j.tet.2004.10.025

  日期：2004.12

  Using the Pictet–Spengler reactions of tryptophan with aldehydes under acidic conditions at ambient temperature, diastereoisomers of 1,3-disubstituted-1,2,3,4-tetrahydro-β-carbolines could readily be furnished in short time (0.5–4 h) with good to excellent yields (50–98%). Though intrinsically slow in reaction rates, ketone reactions can be accelerated (from days to minutes) using microwaves in open

  使用色氨酸与醛在环境温度下的酸性条件下的Pictet-Spengler反应，可以轻松地在短时间内（0.5–4小时）提供1,3-二取代-1,2,3,4-四氢-β-咔啉的非对映异构体），具有良好至极佳的收率（50–98％）。尽管反应速度本质上很慢，但在开放的容器中使用微波可以加速酮的反应（从几天到几分钟），分离产率高（67-99％），这使这些咔啉成为合成天然和非天然吲哚生物碱的可行反应中间体。 。简要讨论了两种吲哚生物碱的制备，即四氢-β-咔啉二酮哌嗪和四氢-β-咔啉乙内酰脲。
• Convergent Synthesis of Complex Diketopiperazines Derived from Pipecolic Acid Scaffolds and Parallel Screening against GPCR Targets
  作者：Sivaraman Dandapani、Ping Lan、Aaron B. Beeler、Scott Beischel、Athier Abbas、Bryan L. Roth、John A. Porco,、James S. Panek

  DOI：10.1021/jo061758p

  日期：2006.11.1

  A convergent approach to highly functionalized diketopiperazines (DKPs) using enantioenriched pipecolic acids is described. Scandium triflate-catalyzed [4 + 2] aza-annulation was employed to produce stereochemically well-defined building blocks. A resin "catch and release" strategy was devised to convert annulation products to pipecolic acid monomers. Complex diketopiperazines were efficiently assembled utilizing one-pot cyclodimerization of pipecolic acids. Massively parallel screening of the complex DKPs against a panel of molecular targets identified novel ligands for a number of G-protein-coupled receptors (GPCRs).
• <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.
• [EN] COMPOSITIONS AND FORMULATIONS OF METHYLERTHRITOL PHOSPHATE PATHWAY INHIBITORS AND USES THEREOF<br/>[FR] COMPOSITIONS ET FORMULATIONS D'INHIBITEURS DE LA VOIE MÉTHYLERTHRITOL PHOSPHATE ET LEURS UTILISATIONS
  申请人：VIRGINIA TECH INTELL PROP

  公开号：WO2016069949A1

  公开（公告）日：2016-05-06

  Described herein are compounds and formulations thereof that can inhibit the methylerythritol phosphate pathway (MEP). Also described herein are methods of making and uses of the compounds and formulations thereof described herein.