ethyl 9-phenylpropyl-1-methyl-β-carboline-3-carboxylate | 799821-75-3

• 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: ethyl 9-phenylpropyl-1-methyl-β-carboline-3-carboxylate
• 英文别名: Ethyl 9-phenylpropyl-1-methyl-beta-carboline-3-carboxylate；ethyl 1-methyl-9-(3-phenylpropyl)pyrido[3,4-b]indole-3-carboxylate
• CAS: 799821-75-3
• 化学式: C₂₄H₂₄N₂O₂
• 分子量: 372.467
• InChiKey: UYIMDXVSXGIMLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  522.6±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 9-phenylpropyl-1-methyl-β-carboline-3-carboxylate 在 manganese(IV) oxide 、 锂硼氢 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.0h， 生成 9-(3-phenylpropyl)-1-methyl-β-carboline-3-carboxaldehyde
  参考文献：
  名称：

  Synthesis and preliminary evaluation of novel alkyl diamine linked bivalent β-carbolines as angiogenesis inhibitors

  摘要：

  一系列新颖的双价β-咔啉类化合物被合成并评估为有效的血管生成抑制剂。

  DOI：

  10.1039/c6md00360e
• 作为产物：
  描述：

  1-溴-3-苯基丙烷 在 sodium hydride 、 盐酸 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.08h， 以75%的产率得到ethyl 9-phenylpropyl-1-methyl-β-carboline-3-carboxylate
  参考文献：
  名称：

  HARMINE DERIVATIVES, INTERMEDIATES USED IN THEIR PREPARATION, PREPARATION PROCESSES AND USE THEREOF

  摘要：

  公开号：

  EP1634881B1

文献信息

• Harmine derivatives, intermediates used in their preparations, preparation processes and use therefo
  申请人：Wu Jialin

  公开号：US20090227619A1

  公开（公告）日：2009-09-10

  This invention relates to compounds of general formula (I), wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the specification; intermediates used in their preparation, preparation processes and use thereof. The present invention produces new harmine derivatives with enhanced antitumour activity and lower nervous system toxicity by structurally modification of the parent structure of β-carboline of harmines at position 1, 2, 3, 7 and 9. The compounds of the present invention can be prepared easily with high yield. They can be used in manufacture of a variety of antitumour medicines and medicines used in treatment of tumour diseases in combination of light or radiation therapy.

  本发明涉及一般式（I）的化合物，其中R1、R2、R3、R4和R5如规范中所定义；用于它们的制备的中间体，制备方法和使用。本发明通过在β-噻吩类似物的母体结构的1、2、3、7和9位进行结构修饰，产生具有增强抗肿瘤活性和较低神经系统毒性的新的harmine衍生物。本发明的化合物可以轻松高产制备。它们可以用于制造各种抗肿瘤药物和用于结合光或放射治疗治疗肿瘤疾病的药物。
• Harmine derivatives, intermediates used in their preparations, preparation processes and use thereof
  申请人：Wu Jialin

  公开号：US08772311B2

  公开（公告）日：2014-07-08

  This invention relates to compounds of general formula (I), wherein R1, R2, R3, R4 and R5 are as defined in the specification; intermediates used in their preparation, preparation processes and use thereof. The present invention produces new harmine derivatives with enhanced antitumor activity and lower nervous system toxicity by structurally modification of the parent structure of β-carboline of harmines at position 1, 2, 3, 7 and 9. The compounds of the present invention can be prepared easily with high yield. They can be used in manufacture of a variety of antitumor medicines and medicines used in treatment of tumor diseases in combination of light or radiation therapy.

  本发明涉及通式（I）的化合物，其中R1，R2，R3，R4和R5如规范中所定义；用于其制备的中间体，制备过程以及其用途。本发明通过在β-咔啉毒素的母体结构的1、2、3、7和9位进行结构修饰，产生具有增强的抗肿瘤活性和较低的神经系统毒性的新的哈曼衍生物。本发明的化合物可以轻松地高产制备。它们可以用于制造各种抗肿瘤药物和联合光或放射治疗用于治疗肿瘤疾病的药物。
• Design, synthesis and pharmacological evaluation of β-carboline derivatives as potential antitumor agent via targeting autophagy
  作者：Jingsheng Ao、Feng Zeng、Longhao Wang、Liqin Qiu、Rihui Cao、Xiangpan Li

  DOI：10.1016/j.ejmech.2022.114955

  日期：2023.1

  A series of novel β-carboline derivatives was designed, synthesized and evaluated as potential anticancer agents. Among them, compound 6g showed the most potent antiproliferative activity against the 786–0, HT-29 and 22RV1 cell lines with IC50 values of 2.71, 2.02, and 3.86 μM, respectively. The antitumor efficiency of compound 6g in vivo was also evaluated, and the results revealed that compound 6g

  设计、合成并评估了一系列新型 β-咔啉衍生物作为潜在的抗癌药物。其中，化合物6g对 786-0、HT-29 和 22RV1 细胞系表现出最强的抗增殖活性，IC 50值分别为 2.71、2.02 和 3.86 μM。还评估了化合物6g 在体内的抗肿瘤效率，结果显示化合物6g在小鼠结直肠癌同种移植模型中显着抑制肿瘤发展并减轻肿瘤重量。进一步研究作用机制表明，化合物6g通过刺激 ATG5/ATG7 依赖性自噬途径抑制 HCT116 细胞生长。这些分子可能作为进一步开发结直肠癌治疗药物的候选分子。
• Synthesis and in vitro cytotoxic evaluation of 1,3-bisubstituted and 1,3,9-trisubstituted β-carboline derivatives
  作者：Rihui Cao、Wenlie Peng、Hongsheng Chen、Xuerui Hou、Huaji Guan、Qi Chen、Yan Ma、Anlong Xu

  DOI：10.1016/j.ejmech.2004.11.005

  日期：2005.3

  A series of novel 1,3-bisubstituted and 1, 3,9-trisubstituted beta-carboline derivatives was synthesized from the starting material L-tryptophan. Cytotoxic activities of these compounds were investigated in vitro. The results showed that 1,3,9-trisubstituted beta-carboline derivatives had higher cytotoxic activities in vitro than the corresponding 1,3-bisubstituted compounds. Among all the synthesized 1,3,9-trisubstituted P-carboline derivatives, the compounds with a methyl substituent at position-1 displayed more potent cytotoxic activities, furthermore compound 5e having an ethoxycarbonyl substituent at position-3 and a pentafluorobenzyl at position-9, respectively, was found to be the most potent compounds of this series with IC50 value of 4 uM against BGC-823 cell lines. These data suggested that (1) the cytotoxic potencies of beta-carboline derivatives were enhanced by the introduction of appropriate substituents into position-1 and position-9 in beta-carboline; (2) the beta-carboline structure might be an important basis for the design and synthesis of new antitumor drugs; (3) the methyl substituent at position-1, the pentafluorobenzyl group at position-9 and the ethoxycarbonyl substituent at position-3 were the optimal combination for the improvement of cytotoxic activity of the P-carboline derivatives. (c) 2004 Elsevier SAS. All rights reserved.
• US8772311B2
  申请人：——

  公开号：US8772311B2

  公开（公告）日：2014-07-08