9H-pyrido[3,4-b]indol-1-yl trifluoromethanesulfonate | 154924-05-7

• 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: 9H-pyrido[3,4-b]indol-1-yl trifluoromethanesulfonate
• 英文别名: 1-trifluoromethanesulfonyloxy-β-carboline；1-Trifluormethansulfonyloxy-β-carbolin；1-Trifluoromethanesulfonyloxy-beta-carboline
• CAS: 154924-05-7
• 化学式: C₁₂H₇F₃N₂O₃S
• 分子量: 316.26
• InChiKey: SKQWXGCLAXVMTG-UHFFFAOYSA-N

物化性质

• 沸点：
  483.0±45.0 °C(Predicted)
• 密度：
  1.658±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9H-pyrido[3,4-b]indol-1-yl trifluoromethanesulfonate 在 三氟甲磺酸 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 1.67h， 以76%的产率得到1-iodo-9H-β-carboline
  参考文献：
  名称：

  Synthesis of Alkyl-Substituted Pyridines by Directed Pd(II)-Catalyzed C–H Activation of Alkanoic Amides

  摘要：

  A general alkylation protocol for substituted iodopyridines was developed (32 examples, 44-97% yield). The reaction is based on the Pd(II)-catalyzed C-H activation of 8-aminoquinoline-derived alkanoic amides and it employs a catalyst cocktail of Pd(OAc)(2) (10 mol%), NaI (30 mol%), and (BuO)(2)POOH (20 mol%), with Ag2CO3 as base.

  DOI：

  10.1055/s-0035-1560810
• 作为产物：
  描述：

  色胺 在 吡啶 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 3.5h， 生成 9H-pyrido[3,4-b]indol-1-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Efficient synthesis of eudistomin U and evaluation of its cytotoxicity

  摘要：

  Eudistomin U is a member of a subclass of naturally occurring indole alkaloids known as beta-carbolines. These molecules are reported to have diverse biological activity and high binding affinity to DNA, which make them attractive targets for total synthesis. We describe an efficient, five-step synthesis of eudistomin U by employing two key reactions: a Bischler-Napieralski cyclization and a Suzuki cross coupling. We also describe the cytotoxicity of eudistomin U against various cancer cell lines and human pathogens, in which we observed potent antibacterial activity against Gram-positive bacteria. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.049

文献信息

• [EN] SELECTIVE INHIBITORS OF GENOTOXIC STRESS-INDUCED IKK/NF-kB PATHWAYS<br/>[FR] INHIBITEURS SÉLECTIFS DE VOIES IKK/NF-KB INDUITES PAR LE STRESS GÉNOTOXIQUE
  申请人：MAX DELBRUECK CENTRUM FUER MOLEKULARE MEDIZIN HELMHOLTZ GEMEINSCHAFT

  公开号：WO2018087389A1

  公开（公告）日：2018-05-17

  The invention relates to chemical compounds and their use as a medicament in the treatment of a disease associated with genotoxic stress-induced I KK/NF-κΒ (NF-kappaB) activation, preferably in the treatment of a subject suffering from cancer exhibiting genotoxic stress-induced I KK/NF-κΒ activation. The invention further relates to a pharmaceutical composition comprising a compound of the invention for the treatment of a subject afflicted by a disease associated with genotoxic stress-induced I KK/NF-κΒ activation.

  这项发明涉及化合物及其作为药物在治疗与基因毒性应激诱导的I KK/NF-κΒ（NF-kappaB）激活相关疾病中的用途，优选用于治疗患有展现基因毒性应激诱导的I KK/NF-κΒ激活的癌症患者。该发明还涉及一种包含该发明化合物的药物组合物，用于治疗患有与基因毒性应激诱导的I KK/NF-κΒ激活相关疾病的患者。
• Total Syntheses of β-Carboline Alkaloids Manzamine C, Orthoscuticelline C, and Quassidine S
  作者：Chenchen Zhang、Saiya Liu、Qihua Xiong、Lu Li、Bichu Cheng

  DOI：10.1021/acs.joc.3c02750

  日期：2024.2.2

  hydrofunctionalization reaction of pavettine (4) with various nucleophiles was developed and used as the key step in the total syntheses of β-carboline natural products manzamine C (3), orthoscuticelline C (5), and quassidine S (6). In the 6-step total synthesis of manzamine C (3), an efficient two-step procedure, comprising a Wittig olefination reaction and a Fukuyama–Mitsunobu reaction, was devised for

  开发了帕维汀 ( 4 ) 与各种亲核试剂的区域选择性烯烃氢官能化反应，并将其用作 β-咔啉天然产物曼扎明 C ( 3 )、orthoscuticelline C ( 5 ) 和 quassidine S ( 6 ) 全合成的关键步骤。在曼扎胺 C ( 3 ) 的 6 步全合成中，设计了一种有效的两步程序，包括 Wittig 烯化反应和 Fukuyama-Mitsunobu 反应，用于用Z -烯烃合成N -大环。
• SELECTIVE INHIBITORS OF GENOTOXIC STRESS-INDUCED IKK/NF-KB PATHWAYS
  申请人：Max-Delbrück-Centrum für Molekulare Medizin in der Helmholtz-Gemeinschaft

  公开号：EP3321264A1

  公开（公告）日：2018-05-16

  The invention relates to chemical compounds and their use as a medicament in the treatment of a disease associated with genotoxic stress-induced IKK/NF-κB (NF-kappaB) activation. The invention further relates to a pharmaceutical composition comprising a compound of the invention for the treatment of a subject afflicted by a disease associated with genotoxic stress-induced IKK/NF-κB activation.

  本发明涉及化合物及其在治疗与基因毒性应激诱导的 IKK/NF-κB（NF-kappaB）激活相关的疾病中作为药物的用途。本发明进一步涉及一种包含本发明化合物的药物组合物，用于治疗受基因毒性应激诱导的IKK/NF-κB活化相关疾病困扰的受试者。
• Selective inhibitors of gentotoxic steress-induced IKK/NF-κB pathways
  申请人：Max-Delbrück-Centrum für Molekulare Medizin in der Helmholtz-Gemeinschaft

  公开号：US11028084B2

  公开（公告）日：2021-06-08

  A method is for treatment of a disease associated with genotoxic stress-induced inhibitor of nuclear factor-κB kinase/nuclear factor kappa-light chain enhancer of activated B cells (IKK/NF-κB) signaling. The method can include administering a compound to a subject having a cancer exhibiting genotoxic stress induced IKK/NF-κB activation.

  一种方法用于治疗与基因毒性应激诱导的核因子-κB激酶/活化B细胞的核因子卡巴轻链增强子（IKK/NF-κB）信号转导抑制有关的疾病。该方法可包括向患有基因毒性应激诱导的IKK/NF-κB活化的癌症的受试者施用一种化合物。
• Bracher; Hildebrand, Pharmazie, 1995, vol. 50, # 3, p. 182 - 183
  作者：Bracher、Hildebrand

  DOI：——

  日期：——