methyl 1-(4-methoxybenzoyl)-9H-pyrido[3,4-b]indole-3-carboxylate | 65474-83-1

• 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-methoxybenzoyl)-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 65474-83-1
• 化学式: C₂₁H₁₆N₂O₄
• 分子量: 360.369
• InChiKey: YHARCPCDLXXHRF-UHFFFAOYSA-N

物化性质

• 沸点：
  626.2±55.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  81.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-methoxybenzoyl)-9H-pyrido[3,4-b]indole-3-carboxylate 在 甲醇 、 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  CN116969938

  摘要：

  公开号：
• 作为产物：
  描述：

  4-甲氧基苯乙烯 在 碘 、 二甲基亚砜 、 2-碘酰基苯甲酸 作用下， 生成 methyl 1-(4-methoxybenzoyl)-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Unexplored reactivity of 2-oxoaldehydes towards Pictet–Spengler conditions: concise approach to β-carboline based marine natural products

  摘要：

  在Pictet–Spengler条件下，开发了色氨酸甲酯/色胺与2-氧代醛之间的新型反应，并成功应用于Merinacarboline（A和B）、Eudistomin Y1、Pityriacitrin B、Pityriacitrin、Fascaplysin及其类似物的全合成。

  DOI：

  10.1039/c4ra01387e

文献信息

• Photoredox Generated Vinyl Radicals: Synthesis of Bisindoles and β-Carbolines
  作者：Neha Chalotra、Ajaz Ahmed、Masood Ahmad Rizvi、Zakir Hussain、Qazi Naveed Ahmed、Bhahwal Ali Shah

  DOI：10.1021/acs.joc.8b02193

  日期：2018.12.7

  A photoredox catalyzed approach enabling use of alkynes as surrogate of 2-oxoaldehydes/1,2-diones is reported. The method overcomes the difficulty associated with application of unsubstituted aliphatic α-oxoaldehydes, which has hitherto limited their general use. Indoles, tryptamine, and tryptophan methyl ester participated in the reaction to give a variety of α-oxo based analogues. Quantum yield investigations

  据报道，光氧化还原催化的方法能够使用炔烃作为2-氧醛/ 1,2-二酮的替代物。该方法克服了与未取代的脂族α-氧醛的施用相关的困难，该困难迄今限制了它们的一般用途。吲哚，色胺和色氨酸甲酯参与了反应，得到了多种基于α-氧代的类似物。量子产率研究支持自由基链机制。
• Iodine catalyzed oxidative C(CO)–C(methyl) bond cleavage in methyl ketones: Application to the synthesis of β-Carboline-3-esters
  作者：Satyanarayana Battula、Narsaiah Battini、Jigar Y. Soni、Keyur M. Pandya

  DOI：10.1016/j.tetlet.2023.154872

  日期：2024.1

  A novel synthesis of substituted β-carboline-3-esters was achieved by the molecular iodine catalyzed reaction of tryptophan methyl ester hydrochlorides with methyl ketones through oxidative C(CO) − C(methyl) bond cleavage. The products in these reactions are similar to those produced in regular Pictet-Spengler reactions of tryptophan methyl esters with analogous aldehyde substrates. Studies revealed

  通过分子碘催化色氨酸甲酯盐酸盐与甲基酮通过氧化C(CO) - C(甲基)键断裂反应，实现了取代β-咔啉-3-酯的新合成。这些反应中的产物与色氨酸甲酯与类似醛底物的常规 Pictet-Spengler 反应中产生的产物相似。研究表明，反应涉及亚胺形成、环化，然后碘催化酮底物甲基的 C(CO)−C(烷基) 键断裂，形成最终化合物。
• 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.
• CN116969939
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  公开号：——

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