janetine | 69754-02-5

• 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: janetine
• 英文别名: 1,5-dimethyl-2,3,4,6-tetrahydro-1H-pyrido[4,3-b]carbazole
• CAS: 69754-02-5
• 化学式: C₁₇H₁₈N₂
• 分子量: 250.343
• InChiKey: APVAKFARJVJSTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-O-benzyl 6-O-tert-butyl 5-methyl-3,4-dihydro-1H-pyrido[4,3-b]carbazole-2,6-dicarboxylate 在 manganese(IV) oxide 、 20% palladium hydroxide-activated charcoal 、 氢气 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 75.5h， 生成 janetine
  参考文献：
  名称：

  使用铜介导的 6π-电环化简明全合成吡啶并[4,3-b]咔唑生物碱

  摘要：

  9-甲氧基玫瑰树碱、3,4-二氢玫瑰树碱（μ-生物碱D）、1,2,3,4-四氢玫瑰树碱、2-甲基-1,2,3,4-四氢玫瑰树碱、橄榄树碱、3,4-二氢玫瑰树碱的简明合成、(±)-guatambuine 和 (±)-janetine 是从己三烯中间体开发出来的，这些中间体很容易通过 Pd 催化的吲哚基硼酸盐串联环化/交叉偶联反应获得。该路线通过Cu催化的6π-电环化和随后将吡啶并[4,3-b]咔唑中间体转化为吡啶并[4,3-b]咔唑生物碱，可以轻松构建吡啶并[4,3-b]咔唑。

  DOI：

  10.1002/ejoc.201600246

文献信息

• Synthesis and cytotoxicity of pyrido[4,3-b]carbazole alkaloids against HCT-116 and HL-60 cells
  作者：Tomoki Itoh、Noriyuki Hatae、Takashi Nishiyama、Tominari Choshi、Satoshi Hibino、Teruki Yoshimura、Minoru Ishikura

  DOI：10.1007/s00044-017-2068-6

  日期：2018.2

  known about the biological activities of these compounds. Six synthetic natural alkaloids and five of their derivatives were evaluated for their antiproliferative activity against HCT-116 and HL-60 cells. The activities of variants with the D-reduced ring or without the C(11)-Me group were lower than those of ellipticine. The conformer of guatambuine showed higher activities than guatambuine.

  通过钯催化的串联环化/交叉偶联反应作为关键步骤，合成了玫瑰树碱，奥利福因及其五个还原的天然变异体。另外，通过在茉莉花碱中D环的构象转化获得了先前未知的茉莉花碱构象物。由于几乎没有用于减少天然变异体的合成方法，因此对这些化合物的生物学活性知之甚少。评价了六种合成天然生物碱及其五种衍生物对HCT-116和HL-60细胞的抗增殖活性。具有D还原环或没有C（11）-Me组的变体的活性低于玫瑰树碱。guatambuine的构象异构体显示出比guatambuine高的活性。
• INDOLE CONTAINING SMALL CHEMICAL COMPOUNDS AND USE THEREOF FOR THE NON-CYTOTOXIC AND IMMUNOLOGICAL TREATMENT OF CANCER
  申请人：AC BioScience SA

  公开号：EP3714883A1

  公开（公告）日：2020-09-30

  The invention provides an indole-containing compound able to induce actin network remodeling in cancer cells into actin organized network and use thereof in non-cytotoxic cancer immunotherapy, for enhancing immune checkpoint inhibitor therapy, for activating cancer immune response, for treating or lessening the symptoms of, or preventing the human cancer, alone or in combination with one or more cancer immunotherapeutic agent for simultaneous, separate or sequential administration.

  本发明提供了一种能够诱导癌细胞肌动蛋白网络重塑为肌动蛋白有序网络的含吲哚化合物及其在非细胞毒性癌症免疫疗法中的用途，用于增强免疫检查点抑制剂疗法、激活癌症免疫反应、治疗或减轻人类癌症症状或预防癌症，可单独或与一种或多种癌症免疫治疗剂联合使用，可同时、单独或连续给药。
• Beta-Carboline Compounds And Use Thereof For The Non-Cytotoxic And Immunological Treatment Of Cancer
  申请人：AC BIOSCIENCE SA

  公开号：US20220142994A1

  公开（公告）日：2022-05-12

  The invention provides a β-carboline compound (an indole-containing compound) able to induce actin network remodeling in cancer cells into actin organized network and use thereof in non-cytotoxic cancer immunotherapy, for enhancing immune checkpoint inhibitor therapy, for activating cancer immune response, for treating or lessening the symptoms of, or preventing the human cancer, alone or in combination with one or more cancer immunotherapeutic agent for simultaneous, separate or sequential administration.
• [EN] BETA-CARBOLINE COMPOUNDS AND USE THEREOF FOR THE NON-CYTOTOXIC AND IMMUNOLOGICAL TREATMENT OF CANCER<br/>[FR] COMPOSÉS DE BÊTA-CARBOLINE ET LEUR UTILISATION POUR LE TRAITEMENT NON CYTOTOXIQUE ET IMMUNOLOGIQUE DU CANCER
  申请人：AC BIOSCIENCE SA

  公开号：WO2020193502A1

  公开（公告）日：2020-10-01

  The invention provides a β-carboline compound (an indole-containing compound)able to induce actin network remodeling in cancer cells into actin organized network and use thereof in non-cytotoxic cancer immunotherapy, for enhancing immune checkpoint inhibitor therapy, for activating cancer immune response, for treating or lessening the symptoms of, or preventing the human cancer, alone or in combination with one or more cancer immunotherapeutic agent for simultaneous, separate or sequential administration.
• [EN] IMMUNOMODULATORY COMPOUNDS AND USE THEREOF FOR THE TREATMENT AND/OR PREVENTION OF INFECTIOUS DISEASES<br/>[FR] COMPOSÉS IMMUNOMODULATEURS ET LEUR UTILISATION POUR LE TRAITEMENT ET/OU LA PRÉVENTION DE MALADIES INFECTIEUSES
  申请人：[en]AC BIOSCIENCE SA

  公开号：WO2022063858A1

  公开（公告）日：2022-03-31

  The invention provides immunomodulatory compounds, adjuvant compositions comprising thereof, immunogenic compositions comprising thereof and uses of immunomodulatory compounds as adjuvants in vaccination, for increasing the immune response via the improvement of maturation and activation of dendritic cells, and for the treatment and/or prevention of infectious diseases, cancer and autoimmune diseases.