1-(1-hydroxyethyl)-β-carboline | 148683-93-6

• 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: 1-(1-hydroxyethyl)-β-carboline
• 英文别名: 1-(9H-pyrido[3,4-b]indol-1-yl)ethan-1-ol；Cordysinin C/D；1-(9H-pyrido[3,4-b]indol-1-yl)ethanol
• CAS: 148683-93-6
• 化学式: C₁₃H₁₂N₂O
• 分子量: 212.251
• InChiKey: GKXWQOGSNJJLKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-hydroxyethyl)-β-carboline 在 manganese(IV) oxide 、 戴斯-马丁氧化剂 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 以70%的产率得到1-(9H-beta-咔啉-1-基)乙酮
  参考文献：
  名称：

  新型荧光硼-β-咔啉染料的合成与表征

  摘要：

  新的荧光硼-β-咔啉家族的第一个代表是通过将二氟硼基基团插入恶氮杂或二氮杂核而合成的。所得化合物表现出良好的光物理性质，在 38-85 nm 范围内具有良好的斯托克斯位移，具有蓝色和绿色发射。通过量子化学计算研究了两个成员的激发态和分子轨道的能量学，表明二氮杂硼啉基-咔啉相对于氧杂硼并-咔啉具有改进的性能。这些特性提名该化学型作为用于开发荧光探针的新荧光团。例如，二氮杂硼啉-咔啉用于特异性标记抗 Her2 抗体曲妥珠单抗。该荧光缀合物显示出高荧光团-抗体比率，并被证实是体外肿瘤细胞标记和共焦显微镜成像以及肿瘤切片离体双光子显微镜成像的有用工具。

  DOI：

  10.1039/d1ra02132j
• 作为产物：
  描述：

  色胺盐酸盐 在 4-二甲氨基吡啶 、 水 、 二异丁基氢化铝 、 对甲苯磺酸 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 0.5h， 生成 1-(1-hydroxyethyl)-β-carboline
  参考文献：
  名称：

  Synthesis and Evaluation of β-Carbolinium Cations as New Antimalarial Agents Based on π-Delocalized Lipophilic Cation (DLC) Hypothesis

  摘要：

  合成了几种β-卡巴啉，包含天然存在的物质及其相应的阳离子衍生物，并评估了它们的抗疟疾（抗红血球变形虫）活性，包括体外和体内实验。一个四环卡巴啉盐被阐明具有体外抗利什曼病和抗锥虫病活性，以及抗疟疾活性。季铵卡巴啉阳离子在体外表现出比电子中性β-卡巴啉显著更高的效力，并且观察到了π-去局域化的脂溶性阳离子（DLC）结构与抗疟疾效力之间的良好相关性。β-卡巴啉化合物在体内对啮齿动物疟疾表现出中等的抑制活性。

  DOI：

  10.1248/cpb.53.653

文献信息

• Formation, Characterization, and Occurrence of β-Carboline Alkaloids Derived from α-Dicarbonyl Compounds and <scp>l</scp>-Tryptophan
  作者：Tomás Herraiz、Adriana Peña、Haroll Mateo、Marta Herraiz、Antonio Salgado

  DOI：10.1021/acs.jafc.2c03187

  日期：2022.7.27

  occurring bioactive alkaloids, whereas α-dicarbonyl compounds are reactive substances generated in foods and in vivo. In this work, l-tryptophan reacted with α-dicarbonyl compounds affording new β-carbolines. Glyoxal afforded 1-hydroxymethyl-β-carboline (HME-βC) and its 3-carboxylic acid, and methylglyoxal afforded 1-(1-hydroxyethyl)-β-carboline (HET-βC) and its 3-carboxylic acid. 3-Deoxyglucosone afforded

  β-咔啉 (βCs) 是天然存在的生物活性生物碱，而 α-二羰基化合物是食物和体内产生的活性物质。在这项工作中，l-色氨酸与 α-二羰基化合物反应生成新的 β-咔啉。乙二醛提供 1-羟甲基-β-咔啉 (HME-βC) 及其 3-羧酸，甲基乙二醛提供 1-(1-羟乙基)-β-咔啉 (HET-βC) 及其 3-羧酸。3-脱氧葡萄糖酮提供 1-(1,3,4,5-四羟基戊-1-基)-β-咔啉异构体 ( 1a/b ), 1-(1,4,5-三羟基戊-1-基)-β-咔啉 ( 2 ) 和 1-(1,5-dihydroxypent-3-en-1-yl)-β-咔啉 ( 3）。这些βCs的形成在酸性条件下和随着温度的升高而增加。提出了一种机制来解释基于互变异构和环化为二氢-βC-3-COOH 中间体将羰基转化为羟基的机制，将其分离并得到βC。这些α-二羰基衍生的βCs发生在l的模型反应中-色氨酸与果糖或葡萄糖在加热下孵育，可被视为晚期糖基化终产物
• A versatile route to the synthesis of 1-substituted β-carbolines by a single step Pictet–Spengler cyclization
  作者：Mei-Lin Yang、Ping-Chung Kuo、Amooru G. Damu、Ren-Jie Chang、Wen-Fei Chiou、Tian-Shung Wu

  DOI：10.1016/j.tet.2006.08.081

  日期：2006.11

  A one-step conversion of L-tryptophan and activated aldehydes (1,2-dicarbonyl compounds) directly to 1-substituted beta-carbolines without formation of the tetrahydro derivatives under modified Pictet-Spengler conditions was described. Moreover, a practical application for the synthesis of a natural 1-substituted beta-carboline, luzongerine A, isolated from Illigera luzonensis was also successfully carried out utilizing this protocol. The effects of synthetic compounds 11 and 11a on nitric oxide (NO) production in LPS/IFN-gamma stimulated RAW 264.7 macrophage cells were evaluated in vitro. They displayed significant dose-dependent inhibition of inducible nitric oxide synthase (iNOS). (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, in vitro anti-inflammatory and cytotoxic evaluation, and mechanism of action studies of 1-benzoyl-β-carboline and 1-benzoyl-3-carboxy-β-carboline derivatives
  作者：Mei-Lin Yang、Ping-Chung Kuo、Tsong-Long Hwang、Wen-Fei Chiou、Keduo Qian、Chin-Yu Lai、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmc.2011.01.034

  日期：2011.3

  In the present study, various 1-substituted and 1,3-disubstituted beta-carboline derivatives were synthesized by a modified single-step Pictet-Spengler reaction. The compounds were examined for cytotoxicity and anti-inflammatory activity, as measured by the inhibition of prostaglandin E-2 (PGE(2)) production and nitric oxide (NO) production. While only two compounds (28 and 31) showed marginal cytotoxicity against four human cancer cell lines, most of the tested compounds exhibited potent inhibitory activity of both NO and PGE(2) production. Moreover, compounds 6 and 16 significantly reduced the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX2), suggesting that beta-carboline analogs can inhibit NO and PGE(2) production at the translational level. In addition, several of the beta-carboline derivatives (1, 2, 48, 11, 13, 22, 25, 27, 31, and 41-43) displayed significant inhibitory activity of superoxide anion (O-2(center dot-)) generation or elastase release compared to the reference compound, with 6 being the most potent. N-Formyl-L-methionyl-phenylalanine (FMLP)-induced phosphorylation of c-Jun N-terminal kinase (JNK) and protein kinase B (AKT) were also inhibited by 6, suggesting that it suppresses human neutrophil functions by inhibiting the activation of JNK and AKT signaling pathways. Therefore, the synthetic 1-benzoyl-3-carboxy beta-carboline analogs may have great potential to be developed as anti-inflammatory agents. (C) 2011 Elsevier Ltd. All rights reserved.
• The role of methylglyoxal in the non-enzymatic conversion of tryptophan, its methyl ester and tryptamine to 1-acetyl-β-carbolines
  作者：Ina Nemet、Lidija Varga-Defterdarović

  DOI：10.1016/j.bmc.2008.02.039

  日期：2008.4

  Non-enzymatic modi. cation of L-tryptophan ( 1) and its metabolites and derivatives with aldehydes, via the Pictet-Spengler reaction, affords beta-carbolines. Here we demonstrate that methylglyoxal ( 2) generates 1-acetyl-beta-carbolines from tryptophan ( 1), from its methyl ester ( 6) and from tryptamine ( 4); however, 2 did not generate 1-(1-hydroxyethyl)-beta-carboline derivates. HPLC analysis of model reaction systems showed formation of 1-acetyl-beta-carboline ( 3) and 1-acetyl-beta-carboline-3-carboxylic acid ( 5) during incubation of 1 and 2, at pH 5.7 and 7.4, at 100 degrees C, and only 5 at 37 degrees C, at the same pH values, with limited access of oxygen. Aerobic conditions caused higher formation of 3 at 37 degrees C at both pH values, while, at higher temperature, the same effect was only observed at pH5.7. Lack of oxygen did not much influence the formation of 3 or 5 at both pH and temperature values, in comparison with the formation at limited access of oxygen. Incubation of 2 and 6 generated methyl-1-acetyl-beta-carboline-3-carboxylate ( 7) together with 3 and 5 as a result of hydrolysis of 6 into 1 and, partially, 7 into 5, while in incubation mixtures of 2 and 4 only unstable 1-acetyl-3,4-dihydro-beta-carboline ( 8) was observed. Incubation of 1 with D-glucose as well as incubation of tryptophan with Amadori product 18 under similar conditions did not generate carbolines 3 or 5. For the first time, we were able to demonstrate the presence of 1-acetyl-beta-carboline-3-carboxylic acid ( 5) in some commercially available ketchups and in previously heated tomato concentrate. (c) 2008 Elsevier Ltd. All rights reserved.
• Bracher, Franz; Hildebrand, Dirk, Liebigs Annalen der Chemie, 1993, # 8, p. 837 - 840
  作者：Bracher, Franz、Hildebrand, Dirk

  DOI：——

  日期：——