3,9-difluoro-arcyriaflavin A | 118458-59-6

• 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: 3,9-difluoro-arcyriaflavin A
• 英文别名: 7,19-Difluoro-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione
• CAS: 118458-59-6
• 化学式: C₂₀H₉F₂N₃O₂
• 分子量: 361.307
• InChiKey: NVANEXBMGAPUOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5E,6E)-5,6-bis[(4-fluorophenyl)hydrazinylidene]-3a,4,7,7a-tetrahydroisoindole-1,3-dione 以61%的产率得到
  参考文献：
  名称：

  BERGMAN, JAN;PELCMAN, BENJAMIN, J. ORG. CHEM., 54,(1989) N, C. 824-828

  摘要：

  DOI：

文献信息

• Design and Synthesis of a Fluoroindolocarbazole Series as Selective Topoisomerase I Active Agents. Discovery of Water-Soluble 3,9-Difluoro-12,13-dihydro-13-[6-amino-β- <scp>d</scp>-glucopyranosyl]-5<i>H</i>,13<i>H</i>-benzo[<i>b</i>]- thienyl[2,3-<i>a</i>]pyrrolo[3,4-<i>c</i>]carbazole- 5,7(6<i>H</i>)-dione (BMS-251873) with Curative Antitumor Activity against Prostate Carcinoma Xenograft Tumor Model
  作者：Balu N. Balasubramanian、Denis R. St. Laurent、Mark G. Saulnier、Byron H. Long、Carol Bachand、Francis Beaulieu、Wendy Clarke、Milind Deshpande、Jeffrey Eummer、Craig R. Fairchild、David B. Frennesson、Robert Kramer、Frank Y. Lee、Mikael Mahler、Alain Martel、B. Narasimhulu Naidu、William C. Rose、John Russell、Edward Ruediger、Carola Solomon、Karen M. Stoffan、Henry Wong、Kurt Zimmermann、Dolatrai M. Vyas

  DOI：10.1021/jm034197s

  日期：2004.3.1

  A series of fluoroindolocarbazoles were studied with respect to their topoisomerase I activity, cytotoxicity, selectivity, and in vivo antitumor activity. Emerging from this series was BMS-251873, a potential clinical candidate possessing a robust pharmacological profile including curative antitumor activity against prostate carcinoma.

  研究了一系列氟吲哚并咔唑的拓扑异构酶I活性，细胞毒性，选择性和体内抗肿瘤活性。从该系列中诞生的是BMS-251873，这是一种潜在的临床候选药物，具有强大的药理特性，包括对前列腺癌的治愈性抗肿瘤活性。
• A Facile Synthesis of Indolo[2,3-<i>a</i>]pyrrolo[3,4-<i>c</i>]carbazoles via Oxidative Photocyclization of Bisindolylmaleimides
  作者：Biing-Jiun Uang、G. Mahesh Reddy、Shyh-Yeon Chen

  DOI：10.1055/s-2003-37645

  日期：——

  A simple and inexpensive oxidative photocyclization of the bisindolylmaleimides in the presence of a catalytic amount of iodine leading to indolo[2,3-a]pyrrolo[3,4-c]carbazoles in 84-90% yields is described.

  描述了在催化量的碘存在下对双吲哚基马来酰亚胺进行简单且廉价的氧化光环化，从而以 84-90% 的收率生成吲哚 [2,3-a] 吡咯并 [3,4-c] 咔唑。
• Practical synthesis of the rebeccamycin aglycone and related analogs by oxidative cyclization of bisindolylmaleimides with a Wacker-type catalytic system
  作者：Jianji Wang、Miguel Rosingana、Daniel J Watson、Eric D Dowdy、Robert P Discordia、Nachimuthu Soundarajan、Wen-Sen Li

  DOI：10.1016/s0040-4039(01)02021-4

  日期：2001.12

  Using atmospheric O2 as the stoichiometric oxidant, Pd2+/Cu2+-catalyzed oxidative cyclization of the corresponding bisindolylmaleimides provides the rebeccamycin aglycone and related indolo[2,3-a]pyrrolo[3,4-c]carbazoles in 58–88% yield. The method is operationally simple and utilizes readily prepared substrates, making the process amenable to scaleup.

  利用大气Ò 2作为化学计量的氧化剂，钯2+ / Cu的2+催化的氧化相应bisindolylmaleimides的环化提供了利拜卡霉素糖苷配基和相关的吲哚并[2,3-一个]吡咯并[3,4- c ^ ]在58-咔唑产率88％。该方法操作简单，并且利用容易制备的基材，使得该方法适合规模化生产。
• PIM kinase inhibitor compositions, methods, and uses thereof
  申请人：Snap Bio, Inc.

  公开号：US11319320B2

  公开（公告）日：2022-05-03

  This application relates to compounds of formulae (I) and (II) and compositions thereof useful as inhibitors of PIM kinases. Also provided are methods of synthesis and methods of use of PIM inhibitors in treating individuals suffering from cancerous malignancies.

  本申请涉及作为 PIM 激酶抑制剂的式 (I) 和 (II) 化合物及其组合物。还提供了 PIM 抑制剂的合成方法和用于治疗癌症恶性肿瘤患者的方法。
• Synthesis of indolo[2,3-a]pyrrolo[3,4-c]carbazoles by double Fischer indolizations
  作者：Jan Bergman、Benjamin Pelcman

  DOI：10.1021/jo00265a020

  日期：1989.2