8-bromo-β-carboline | 144434-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 8-bromo-β-carboline
• 英文别名: 8-Bromo-9H-pyrido[3,4-b]indole
• CAS: 144434-77-5
• 化学式: C₁₁H₇BrN₂
• 分子量: 247.094
• InChiKey: KLIOMPHXRYNWGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,6-二溴己烷 、 8-bromo-β-carboline 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以37%的产率得到1,6-bis(8-bromo-β-carboline-9-yl)hexane
  参考文献：
  名称：

  ビスβ−カルボリン系化合物、その製造方法、医薬組成物および用途

  摘要：

  This invention discloses bis β-carboline compounds, their manufacturing method, pharmaceutical compositions, and applications. Specifically, the bis β-carboline compounds and their pharmaceutically acceptable salts are represented by general formula I, and are produced by condensation of β-carboline intermediates and dihaloalkanes. Furthermore, the invention discloses pharmaceutical compositions containing the bis β-carboline compounds represented by formula I in effective dosages and pharmaceutically acceptable carriers, as well as applications in the manufacturing of antitumor agents using these bis β-carboline compounds. Such tumors include melanoma, gastric cancer, lung cancer, breast cancer, kidney cancer, liver cancer, oral squamous cell carcinoma, cervical cancer, ovarian cancer, pancreatic cancer, prostate cancer, and colon cancer.【Chemical formula 1】

  公开号：

  JP2016500080A
• 作为产物：
  描述：

  9H-吡啶[3,4-b]吲哚 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以85%的产率得到6-溴-9H-吡啶并[3,4-b]吲哚
  参考文献：
  名称：

  β-咔啉生物碱溴化得到的溴-β-咔啉的合成与分离

  摘要：

  在不同的实验条件下，β-咔啉（1-5）会被N-溴代琥珀酰亚胺进行亲电芳香取代。尽管前段时间通过溴化正六烷（1）溴化获得的6-溴-正六烷（1a）已被分离并完全表征，但正六烷（1b-1e）和harmane（2a-2e）的其他溴代衍生物部分被描述为反应混合物的一部分。报告了1b，1c，1d，1e，2a，2b，2c，2d，2e的制备以及随后的分离，纯化和完整表征（mp，R f，1 H-nmr，13C-nmr和ms）以及从harmine（3a-3e），harmol（4a，4b）和7-乙酰基harmol （5a-5c）获得的溴代衍生物的首次制备，分离和表征。作为溴化剂Ñ溴代琥珀酰亚胺和Ñ溴代琥珀酰亚胺硅胶在二氯甲烷和氯仿中，以及在β咔啉- ñ -bomosuccinimide固体混合物已被用于和其用途进行了比较。进行了半经验的AMI和PM3计算，以便根据HOMO的能量，HOMO-LUMO的差异以及β-

  DOI：

  10.1002/jhet.5570380512

文献信息

• Antimalarial and antitubercular nostocarboline and eudistomin derivatives: Synthesis, in vitro and in vivo biological evaluation
  作者：Simone Bonazzi、Damien Barbaras、Luc Patiny、Rosario Scopelliti、Patricia Schneider、Stewart T. Cole、Marcel Kaiser、Reto Brun、Karl Gademann

  DOI：10.1016/j.bmc.2010.01.013

  日期：2010.2

  The synthesis of nine nostocarboline derivatives with substitutions of the 2-methyl group by alkyl, aryl and functionalized residues, 10 symmetrical bis cationic dimers linking 6-Cl-norharmane through the 2-position and fifteen derivatives of the marine alkaloids eudistomin N and O is reported. These compounds were evaluated in vitro against four parasites (Trypanosoma brucei rhodesiense STIB 900,

  合成了九种二甲基咔啉衍生物，其中2-甲基被烷基，芳基和官能化残基取代； 10个对称的双阳离子二聚体（通过海洋生物碱eudiSTomin N和O的2位连接6-氯正壬烷）和十五种衍生物被合成。报告。这些化合物在体外评价对四名寄生虫（布氏锥虫罗得西亚STIB 900，克氏锥虫Tulahuen C2C4，杜氏利什曼原虫MHOM-ET-67 / L82无菌无鞭毛体，和恶性疟原虫K1株），针对结核分枝杆菌H37Rv的，耻垢分枝杆菌MC 2 155和谷氨酸棒杆菌ATCC13032，并确定了对L6大鼠成肌细胞的细胞毒性。NoSTocarboline及其衍生物显示出对恶性疟原虫的有效且选择性的体外抑制作用，且细胞毒性较弱。二聚体显示的亚微摩尔的抑制杜氏利什曼原虫和布氏锥虫和纳摩尔的活性针对恶性疟原虫，尽管具有显着的细胞毒性。一个二聚体显示出针对结核分枝杆菌的MIC 99值为2.5μg/ ml。烷基化的芥末胺
• A new method for bromination of carbazoles, β-carbolines and iminodibenzyls by use of N-bromosuccinimide and silica gel
  作者：Keith Smith、D.Martin James、Anil G. Mistry、Martin R. Bye、D.John Faulkner

  DOI：10.1016/s0040-4020(01)90362-x

  日期：1992.9

  in high yields at ambient temperature in dichloromethane by use of the appropriate quantity of N-bromosuccinimide in the presence of silica gel. By contrast, the brominations of the β-carbolines, harmane and norharman, are less selective and give mixtures of products, some of which have unusual substitution patterns.

  咔唑，N-乙基咔唑，亚氨基二苄基（10,11-二氢-5H-二苯并[b，f] a庚因），N-乙基亚氨基二苄基和丙咪嗪在环境温度下很容易在二氯甲烷中以高收率单溴，二溴或多溴化在硅胶存在下适量的N-溴琥珀酰亚胺。相比之下，β-咔啉，harmane和Norharman的溴化选择性较低，并产生产物混合物，其中一些具有不同寻常的取代模式。
• 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。
• Photocatalytic enantioselective Minisci reaction of β-carbolines and application to natural product synthesis
  作者：Mu-Peng Luo、Yi-Jie Gu、Shou-Guo Wang

  DOI：10.1039/d2sc05313f

  日期：——

  A highly efficient enantioselective direct C–H functionalization of β-carbolines via a Minisci-type radical process under a photo-redox and chiral phosphoric acid cooperative catalytic system has been disclosed. Through this protocol, a wide range of C1 aminoalkylated β-carbolines were constructed directly with high levels of enantioselectivities from readily available β-carbolines and alanine-derived

  β-咔啉的高效对映选择性直接 C-H 官能化已经公开了在光氧化还原和手性磷酸协同催化体系下的Minisci型自由基过程。通过该协议，从现成的 β-咔啉和丙氨酸衍生的氧化还原活性酯中直接构建了具有高水平对映选择性的各种 C1 氨基烷基化 β-咔啉。这种转化可以直接获得非常有价值的富含对映体的 β-咔啉，这是有价值的天然产物和合成生物活性化合物中一个有趣的结构基序。该协议已被用作海洋生物碱 eudistomin X、(+)-eudistomidin B 和 (+)-eudistomidin I 的简洁不对称全合成的高效合成策略。
• 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。

表征谱图