marinacarboline B | 1338578-38-3

• 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: marinacarboline B
• 英文别名: 1-acetyl-N-[2-(4-hydroxyphenyl)ethyl]-9H-pyrido[3,4-b]indole-3-carboxamide
• CAS: 1338578-38-3
• 化学式: C₂₂H₁₉N₃O₃
• 分子量: 373.411
• InChiKey: XHHABJFVNYNXCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  95.1
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基苯乙醇 在 bis-triphenylphosphine-palladium(II) chloride 、 氰基磷酸二乙酯 、 氯化铵 、 二硫代磷酸二乙酯 、 三乙胺 、 potassium hydroxide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.75h， 生成 marinacarboline B
  参考文献：
  名称：

  从简单化学品直接合成结构不同的吲哚生物碱

  摘要：

  已开发出一种新颖的底物裂解/环加成策略，可从非常简单的2-乙烯基苯胺，炔烃和TBN直接合成并在结构上多样化的吲哚生物碱，这提供了一种无贵金属的有效方法，可访问高度有价值的吲哚衍生物库包括色胺和色胺相关的肟，内酰胺和内酯，以及β-咔啉，螺二吲哚和六氢吡咯并[2,3- b ]吲哚。

  DOI：

  10.1002/cjoc.201800258

文献信息

• Unexplored reactivity of 2-oxoaldehydes towards Pictet–Spengler conditions: concise approach to β-carboline based marine natural products
  作者：Narsaiah Battini、Anil K. Padala、Nagaraju Mupparapu、Ram A. Vishwakarma、Qazi Naveed Ahmed

  DOI：10.1039/c4ra01387e

  日期：——

  Novel reactions under Pictet–Spengler conditions between tryptophan methyl ester/tryptamine and 2-oxoaldehydes have been developed and successfully utilized for the total synthesis of Merinacarboline (A and B), Eudistomin Y1, Pityriacitrin B, Pityriacitrin, Fascaplysin and analogues.

  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。
• Design, Synthesis, and Biological Activity of Marinacarboline Analogues as STAT3 Pathway Inhibitors for Docetaxel-Resistant Triple-Negative Breast Cancer
  作者：Woong Sub Byun、Hyewon Lim、Junhwa Hong、Eun Seo Bae、Seok Beom Lee、Younggwan Kim、Jeeyeon Lee、Sang Kook Lee、Suckchang Hong

  DOI：10.1021/acs.jmedchem.2c01115

  日期：2023.2.23

  triple-negative breast cancer (mTNBC) is a fatal type of breast cancer (BC), and signal transducer and activator of transcription 3 (STAT3) has emerged as an effective target for mTNBC. In the present study, compound MC0704 was found to be a novel synthetic STAT3 pathway inhibitor, and its potential antitumor activity was demonstrated using in vitro and in vivo models in docetaxel-resistant TNBC cells. Based

  转移性三阴性乳腺癌 (mTNBC) 是一种致命类型的乳腺癌 (BC)，信号转导和转录激活因子 3 (STAT3) 已成为 mTNBC 的有效靶点。在本研究中，化合物MC0704被发现是一种新型合成 STAT3 通路抑制剂，其潜在的抗肿瘤活性在多西紫杉醇耐药的 TNBC 细胞中使用体外和体内模型得到证实。基于 marinacarboline (MC)，合成了一系列 β-咔啉衍生物，并研究了它们对多西紫杉醇耐药 MDA-MB-231 (MDA-MB-231-DTR) 细胞的抗肿瘤活性。结合抗增殖和 STAT3 抑制活性，MC0704被选为最有前途的 β-咔啉化合物。MC0704在体外有效地阻止了 MDA-MB-231-DTR 细胞的转移潜能，并且MC0704和多西他赛的组合在异种移植小鼠模型中表现出有效的抗肿瘤活性。这些发现表明，MC0704可以作为具有多西紫杉醇耐药性的 TNBC 患者的靶向治疗药物的主要候选药物。
• An efficient synthesis method targeted to marine alkaloids marinacarbolines A–D and their antitumor activities
  作者：Jun Li、Yang Tang、Hui-Juan Jin、Yi-Di Cui、Li-Juan Zhang、Tao Jiang

  DOI：10.1080/10286020.2014.1003049

  日期：2015.3.4

  Marinacarbolines A-D are a series of marine beta-carboline alkaloids isolated from actinomycete Marinactinospora thermotolerans of the deep South China Sea with antiplasmodial activities. In inhibition assays of in vitro growth of Plasmodium falciparum, marinacarbolines exhibited antiplasmodial activity against drug-sensitive line 3D7 and drug-resistant line Dd2 of P. falciparum. However, approaches for the synthesis of such useful compounds are very limited. In this work, we reported a simple, efficient, and versatile process to synthesize marinacarbolines A-D (1-4). On the basis of that, the antitumor activities of marinacarbolines in a structure-dependent manner were allowed to be unveiled.
• First Total Syntheses of 1,3-Disubstituted β-Carboline Alkaloids, Dichotomide I and Marinacarbolines A-D
  作者：Satoshi Hibino、Tominari Choshi、Shinji Tagawa、Asuka Okamoto、Takashi Nishiyama、Shiroh Watanabe、Noriyuki Hatae

  DOI：10.3987/com-12-12630

  日期：——

  The first total syntheses of dichotomide I (1), and marinacarbolines A-D (3-6) were achieved in four steps from methyl 1-chloro-beta-carboline-3-carboxlyate (9), which was previously used as a synthetic intermediate of dichotomine C. The required compound 9 was prepared in a six-step sequence including a microwave-assisted thermal electrocyclic reaction of a 1-azahexatriene system.