1,6-bis(7-methoxy-1-methyl-β-carboline-9-yl)hexane | 1415723-55-5

• 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: 1,6-bis(7-methoxy-1-methyl-β-carboline-9-yl)hexane
• 英文别名: 7-Methoxy-9-[6-(7-methoxy-1-methylpyrido[3,4-b]indol-9-yl)hexyl]-1-methylpyrido[3,4-b]indole；7-methoxy-9-[6-(7-methoxy-1-methylpyrido[3,4-b]indol-9-yl)hexyl]-1-methylpyrido[3,4-b]indole
• CAS: 1415723-55-5
• 化学式: C₃₂H₃₄N₄O₂
• 分子量: 506.648
• InChiKey: QHLWPKPMAVWKLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,6-二溴己烷 、 肉叶云香碱 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以45%的产率得到1,6-bis(7-methoxy-1-methyl-β-carboline-9-yl)hexane
  参考文献：
  名称：

  Design, synthesis and in vitro and in vivo antitumor activities of novel bivalent β-carbolines

  摘要：

  A series of bivalent beta-carbolines with a spacer of three to ten methylene units between the indole nitrogen was synthesized and evaluated as antitumor agents. The results demonstrated that compounds 18c, 21b, 25a and 31b exhibited strong cytotoxic activities with IC50 value of lower than 20 mu M against four tumor cell lines. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated, compounds 18b, 21b, 26a and 31b exhibited potent antitumor activities with tumor inhibition rate of over 40% in animal models. Preliminary structure-activity relationships analysis indicated that (1) the spacer length affected antitumor potencies, and four to six methylene units were more favorable; (2) the introduction of appropriate substituent into position-1 of beta-carboline facilitated antitumor potencies. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.033

文献信息

• BIS-B-CARBOLINE COMPOUND AND PREPARATION METHOD, PHARMACEUTICAL COMPOSITION AND USE THEREOF
  申请人：XINJIANG HUASHIDAN PHAR MACEUTICAL RESEARCH CO., LTD

  公开号：US20160039845A1

  公开（公告）日：2016-02-11

  Disclosed in the present invention are a bis-β-carboline compound and a preparation method, a pharmaceutical composition and the use thereof. In particular, the bis-β-carboline compound and a pharmaceutical salt thereof are described as general formula I, and the bis-β-carboline compound is prepared through the condensation of β-carboline intermediate and dihaloalkane. Also disclosed in the present invention are a pharmaceutical composition comprising an effective dose of the bis-β-carboline compound as shown in formula I and a pharmaceutically acceptable carrier, and the use of the bis-β-carboline compound in preparing drugs resistant to tumours such as melanoma, stomach cancer, lung cancer, breast cancer, kidney cancer, liver cancer, oral epidermoid carcinoma, cervical cancer, ovarian cancer, pancreatic cancer, prostate cancer, and colon cancer.

  本发明公开了一种双β-咔唑化合物及其制备方法、药物组合物及其用途。其中，描述了双β-咔唑化合物及其药物盐的一般式I，双β-咔唑化合物是通过β-咔唑中间体和二卤代烷的缩合反应制备而成。本发明还公开了一种药物组合物，包括一定剂量的公式I所示的双β-咔唑化合物和药学上可接受的载体，并且公开了将双β-咔唑化合物用于制备对肿瘤具有抗药性的药物，如黑色素瘤、胃癌、肺癌、乳腺癌、肾癌、肝癌、口腔表皮癌、宫颈癌、卵巢癌、胰腺癌、前列腺癌和结肠癌。
• Bis-β-carboline compound and preparation method, pharmaceutical composition and use thereof
  申请人：XINJIANG HUASHIDAN PHARMACEUTICAL RESEARCH CO., LTD.

  公开号：US10011614B2

  公开（公告）日：2018-07-03

  Disclosed in the present invention are a bis-β-carboline compound and a preparation method, a pharmaceutical composition and the use thereof. In particular, the bis-β-carboline compound and a pharmaceutical salt thereof are described as general formula I, and the bis-β-carboline compound is prepared through the condensation of β-carboline intermediate and dihaloalkane. Also disclosed in the present invention are a pharmaceutical composition comprising an effective dose of the bis-β-carboline compound as shown in formula I and a pharmaceutically acceptable carrier, and the use of the bis-β-carboline compound in preparing drugs resistant to tumors such as melanoma, stomach cancer, lung cancer, breast cancer, kidney cancer, liver cancer, oral epidermoid carcinoma, cervical cancer, ovarian cancer, pancreatic cancer, prostate cancer, and colon cancer.

  本发明公开了一种双-β-咔啉化合物及其制备方法、药物组合物和用途。其中，双-β-咔啉化合物及其药用盐描述为通式 I，双-β-咔啉化合物是通过 β-咔啉中间体和二卤代烷烃缩合制备的。本发明还公开了一种药物组合物，该组合物包含有效剂量的式 I 所示的双-β-咔啉化合物和药学上可接受的载体，以及双-β-咔啉化合物在制备抗肿瘤药物中的用途，如黑色素瘤、胃癌、肺癌、乳腺癌、肾癌、肝癌、口腔表皮癌、宫颈癌、卵巢癌、胰腺癌、前列腺癌和结肠癌。
• Design, synthesis and in vitro and in vivo antitumor activities of novel bivalent β-carbolines
  作者：Buxi Shi、Rihui Cao、Wenxi Fan、Liang Guo、Qin Ma、Xuemei Chen、Guoxian Zhang、Liqin Qiu、Huacan Song

  DOI：10.1016/j.ejmech.2012.11.033

  日期：2013.2

  A series of bivalent beta-carbolines with a spacer of three to ten methylene units between the indole nitrogen was synthesized and evaluated as antitumor agents. The results demonstrated that compounds 18c, 21b, 25a and 31b exhibited strong cytotoxic activities with IC50 value of lower than 20 mu M against four tumor cell lines. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated, compounds 18b, 21b, 26a and 31b exhibited potent antitumor activities with tumor inhibition rate of over 40% in animal models. Preliminary structure-activity relationships analysis indicated that (1) the spacer length affected antitumor potencies, and four to six methylene units were more favorable; (2) the introduction of appropriate substituent into position-1 of beta-carboline facilitated antitumor potencies. (C) 2012 Elsevier Masson SAS. All rights reserved.