methyl 1-(3-nitrophenyl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylate | 528524-76-7

• 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-(3-nitrophenyl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylate
• 英文别名: methyl 1-(3-nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 528524-76-7
• 化学式: C₁₉H₁₇N₃O₄
• 分子量: 351.362
• InChiKey: WTZMWVYGTPUZFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 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：
  99.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 1-(3-nitrophenyl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylate 在 二甲基亚砜 作用下， 以40%的产率得到methyl 1-(3-nitrophenyl)-9H-β-carboline-3-carboxylate
  参考文献：
  名称：

  二甲基亚砜将1-芳基（杂芳基）-1,2,3,4-四氢-9 H-β-咔啉-3-羧酸及其酯脱氢

  摘要：

  1-芳基（杂芳基）-1,2,3,4-四氢-9-氧化脱氢Н -β-β-咔啉-3-羧酸的衍生物与二甲亚砜通向1-芳基（杂芳基）-9形成Н - β-咔啉。与脱氢同时发生脱羧。在用甲基1-芳的二甲亚砜（杂芳基）-1,2,3,4-四氢-9-氧化Н -β-β-咔啉-3- carboxylicates甲基-1-芳基（杂芳基）-9- Н -β咔啉形成3-羧酸盐，其水解得到相应的1-芳基（杂芳基）-9Н -β-咔啉-3-羧酸。

  DOI：

  10.1134/s1070428016110117
• 作为产物：
  描述：

  L-色氨酸 在 硫酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 methyl 1-(3-nitrophenyl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylate
  参考文献：
  名称：

  Synthesis, Antileishmanial Activity and Spin Labeling EPR Studies of Novel β-Carboline-Oxazoline and β-Carboline-Dihydrooxazine Derivatives

  摘要：

  A series of novel 1-(substituted-phenyl)-3-(4,5-dihydro-1,3-oxazol-2-yl)-9H-beta-carboline (8a-8i) and 1-(substituted-phenyl)-3-(5,6-dihydro-4H-1,3-oxazin-2-yl)-9H-beta-carboline (9a-9h) derivatives. as well as their respective N-(chloroalkyl)-1-(substituted-phenyl)-9H-beta-carboline-3-carboxamide precursors (6a-6i and 7a-7h), were synthesized and evaluated for their in vitro antileishmanial activity against promastigote and intracellular amastigote forms of Leishmania amazonensis. Compounds 8d. 8i, 9e and 9h exhibited significant activity for both promastigote and amastigote forms, with IC50 (50% inhibitory concentration) values ranging from 2.9 to 23.0 mu M. In addition, spin label electron paramagnetic resonance (EPR) spectroscopy studies were carried out for the most active compounds against L amazonensis promastigotes. The studies indicated that the tested compounds cause strong stiffness in the parasite plasma membrane and are capable of inducing internal metalloproteins oxidation of the parasite, resulting in their cross-linking to skeletal proteins. Compounds 8d and 8i produced the largest effect, showing that the presence of oxazoline group at C-3 of beta-carboline nucleus is important for antileishmanial activity.

  DOI：

  10.21577/0103-5053.20200003

文献信息

• [EN] CARBOLINE AND BETACARBOLINE DERIVATIVES FOR USE AS HDAC ENZYME INHIBITORS<br/>[FR] DERIVES DE CARBOLINE ET DE BETACARBOLINE INHIBITEURS DE L'ENZYME HDAC
  申请人：CHROMA THERAPEUTICS LTD

  公开号：WO2004113336A1

  公开（公告）日：2004-12-29

  Compounds of formula (IA) and (IB) are inhibitors of histone deacetylase activity and useful for the treatment of, inter alia, cancers: wherein fused rings A1 and A2 are optionally substituted; linker radical R1 represents a radical of formula

  式（IA）和（IB）的化合物是组蛋白去乙酰化酶活性的抑制剂，用于治疗癌症等疾病：其中融合的环A1和A2可以选择性地被取代；连接基团R1代表一个公式的基团。
• Dehydrogenation of 1-aryl(hetaryl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acids and their esters with dimethyl sulfoxide
  作者：M. G. Abramyants、D. A. Lomov、T. I. Zavyazkina

  DOI：10.1134/s1070428016110117

  日期：2016.11

  boline-3-carboxylic acids derivatives with dimethyl sulfoxide leads to the formation of 1-aryl(hetaryl)-9Н-β-carbolines. Simultaneously with the dehydrogenation decarboxylation occurs. At the oxidation with dimethyl sulfoxide of methyl 1-aryl (hetaryl)-1,2,3,4-tetrahydro-9Н-β-carboline-3-carboxylicates methyl 1-aryl(hetaryl)-9Н-β-carboline-3-carboxylates formed whose hydrolysis afforded the corresponding

  1-芳基（杂芳基）-1,2,3,4-四氢-9-氧化脱氢Н -β-β-咔啉-3-羧酸的衍生物与二甲亚砜通向1-芳基（杂芳基）-9形成Н - β-咔啉。与脱氢同时发生脱羧。在用甲基1-芳的二甲亚砜（杂芳基）-1,2,3,4-四氢-9-氧化Н -β-β-咔啉-3- carboxylicates甲基-1-芳基（杂芳基）-9- Н -β咔啉形成3-羧酸盐，其水解得到相应的1-芳基（杂芳基）-9Н -β-咔啉-3-羧酸。
• Room-Temperature Aromatization of Tetrahydro-β-carbolines by 2-Iodoxybenzoic Acid: Utility in a Total Synthesis of Eudistomin U
  作者：Joseph D. Panarese、Stephen P. Waters

  DOI：10.1021/ol101688x

  日期：2010.9.17

  2-Iodoxybenzoic acid is a convenient reagent for the dehydrogenation of tetrahydro-beta-carbolines to their aromatic forms under mild conditions. The utility of the method was demonstrated in a total synthesis of the marine indole alkaloid eudistomin U.
• Kumar, Shiv; Roy, Jalpana; Seth, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 1, p. 54 - 59
  作者：Kumar, Shiv、Roy, Jalpana、Seth, M.、Bhaduri, A. P.

  DOI：——

  日期：——
• Synthesis, Antileishmanial Activity and Spin Labeling EPR Studies of Novel β-Carboline-Oxazoline and β-Carboline-Dihydrooxazine Derivatives
  作者：Paula Baréa、Jéssica de Paula、Laís Alonso、Aline de Oliveira、Willian da Costa、Antonio Alonso、Celso Nakamura、Maria Sarragiotto

  DOI：10.21577/0103-5053.20200003

  日期：——

  A series of novel 1-(substituted-phenyl)-3-(4,5-dihydro-1,3-oxazol-2-yl)-9H-beta-carboline (8a-8i) and 1-(substituted-phenyl)-3-(5,6-dihydro-4H-1,3-oxazin-2-yl)-9H-beta-carboline (9a-9h) derivatives. as well as their respective N-(chloroalkyl)-1-(substituted-phenyl)-9H-beta-carboline-3-carboxamide precursors (6a-6i and 7a-7h), were synthesized and evaluated for their in vitro antileishmanial activity against promastigote and intracellular amastigote forms of Leishmania amazonensis. Compounds 8d. 8i, 9e and 9h exhibited significant activity for both promastigote and amastigote forms, with IC50 (50% inhibitory concentration) values ranging from 2.9 to 23.0 mu M. In addition, spin label electron paramagnetic resonance (EPR) spectroscopy studies were carried out for the most active compounds against L amazonensis promastigotes. The studies indicated that the tested compounds cause strong stiffness in the parasite plasma membrane and are capable of inducing internal metalloproteins oxidation of the parasite, resulting in their cross-linking to skeletal proteins. Compounds 8d and 8i produced the largest effect, showing that the presence of oxazoline group at C-3 of beta-carboline nucleus is important for antileishmanial activity.