6-bromo-2,3,4,9-tetrahydro-β-carbolin-1-one | 145489-90-3

• 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: 6-bromo-2,3,4,9-tetrahydro-β-carbolin-1-one
• 英文别名: 6-Bromo-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one；6-bromo-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
• CAS: 145489-90-3
• 化学式: C₁₁H₉BrN₂O
• mdl: MFCD00227125
• 分子量: 265.109
• InChiKey: PRAZBPXVGIVRCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-2,3,4,9-tetrahydro-β-carbolin-1-one 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 6-bromo-N-phenylacetyl-1,3,4,9-tetrahydro-β-carboline
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Tetrahydro-β-carboline Derivatives as Antitumor Growth and Metastasis Agents through Inhibiting the Transforming Growth Factor-β Signaling Pathway

  摘要：

  The transforming growth factor beta (TGF beta) signaling cascade is considered as one of the pivotal oncogenic pathways in most advanced cancers. Inhibition of the TGF beta signaling pathway by specific antagonists, neutralizing antibodies, or small molecules is considered as an effective strategy for the treatment of tumor growth and metastasis. Here we demonstrated the identification of a series of tetrahydro-beta-carboline derivatives from virtual screening which potentially inhibit the TGF beta signaling pathway. Optimization of the initial hit compound 2-benzoyl-1,3,4,9-tetrahydro-beta-carboline (8a) through substitution at different positions to define the structure-activity relationship resulted in the discovery of potent inhibitors of the TGF beta signaling pathway. Among them, compound 8d, one of the tested compounds, not only showed potent inhibition of lung cancer cell proliferation and migration in vitro but also strongly suppressed growth of lung cancer and breast cancer in vivo.

  DOI：

  10.1021/jm401117t
• 作为产物：
  描述：

  4-溴苯胺 在 盐酸 、 甲酸 、 sodium nitrite 作用下， 反应 1.0h， 生成 6-bromo-2,3,4,9-tetrahydro-β-carbolin-1-one
  参考文献：
  名称：

  Synthesis and cytotoxic activity of novel quinazolino-β-carboline-5-one derivatives

  摘要：

  A novel series of quinazolino-beta-carbolinone derivatives was synthesized and evaluated for their in vitro and in vivo anticancer activity. Many compounds have shown good in vitro activity in the range 1-8 muM concentration. Three of the compounds were further tested in nude mice bearing HT-29 colon cancer xenografts. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.005

文献信息

• [EN] BETA-CARBOLINE SULPHONYLUREA DERIVATIVES AS EP4 RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS DE BÊTA-CARBOLINE SULFONYLURÉE EN TANT QU'ANTAGONISTES DU RÉCEPTEUR D'EP4
  申请人：MERCK FROSST CANADA LTD

  公开号：WO2010034110A1

  公开（公告）日：2010-04-01

  The invention is directed to ß-carboline sulphonylurea derivatives as EP4 receptor antagonists useful for the treatment of EP4 mediated diseases or conditions, such as acute and chronic pain, inflammation, osteoarthritis, and rheumatoid arthritis. Pharmaceutical compositions and methods of use are also included.

  该发明涉及ß-咔啉磺酰脲衍生物作为EP4受体拮抗剂，用于治疗EP4介导的疾病或症状，如急性和慢性疼痛、炎症、骨关节炎和类风湿性关节炎。药物组合物和使用方法也包括在内。
• [EN] TETRAHYDRO-BETA-CARBOLINONE DERIVATIVES AND PROCESS FOR PREPARING THE SAME<br/>[FR] DERIVES DE TETRAHYDRO-BETA-CARBOLINONE ET PROCEDE PERMETTANT DE LES PREPARER
  申请人：C & C RES LAB

  公开号：WO2006011750A1

  公开（公告）日：2006-02-02

  The present invention relates to a new tetrahydro-beta-carbolinone derivative having antagonist effect for cyclin dependent kinase as well as an agonist effect for the expression of endogenous tumor suppressor proteins. The present invention also relates to a composition for the treatment of cancer, autoimmune disease, cardio-vascular disease, chemotherapy-induced alopecia and mucositis, infection disease, kidney disease, chronic and acute neurodegenerative disease, and viral infection, comprising the tetrahydro-beta-carbolinone derivative as an active ingredient.

  本发明涉及一种新的四氢-β-咔唑酮衍生物，具有对细胞周期依赖性激酶的拮抗作用，以及对内源肿瘤抑制蛋白表达的激动作用。本发明还涉及一种用于治疗癌症、自身免疫疾病、心血管疾病、化疗诱导的脱发和口腔炎、感染性疾病、肾脏疾病、慢性和急性神经退行性疾病以及病毒感染的组合物，包括四氢-β-咔唑酮衍生物作为活性成分。
• Beta-carboline compounds and analogues thereof as mitogen-activated protein kinase-activated protein kinase-2 inhibitors
  申请人：Anderson R. David

  公开号：US20050137220A1

  公开（公告）日：2005-06-23

  A method is described for inhibiting mitogen activated protein kinase-activated protein kinase-2 in a subject in need of such inhibition, where the method involves administering to the subject a beta-carboline MK-2 inhibiting compound, or a pharmaceutically acceptable salt thereof.

  本文描述了一种用于抑制需要这种抑制的受试者中的有丝分裂原活化蛋白激酶激活蛋白激酶-2的方法，其中该方法涉及向受试者施用一种β-喀啉MK-2抑制化合物或其药学上可接受的盐。
• BETA CARBOLINE SULPHONYLUREA DERIVATIVES AS EP4 RECEPTOR ANTAGONISTS
  申请人：Berthelette Carl

  公开号：US20110275660A1

  公开（公告）日：2011-11-10

  The invention is directed to β-carboline sulphonylurea derivatives as EP4 receptor antagonists useful for the treatment of EP4 mediated diseases or conditions, such as acute and chronic pain, inflammation, osteoarthritis, and rheumatoid arthritis. Pharmaceutical compositions and methods of use are also included.

  这项发明涉及β-咖啡因磺酰脲衍生物作为EP4受体拮抗剂，可用于治疗EP4介导的疾病或病症，如急性和慢性疼痛、炎症、骨关节炎和类风湿性关节炎。还包括制药组合物和使用方法。
• WO2006/58088
  申请人：——

  公开号：——

  公开（公告）日：——