O-methylmahanine | 38826-51-6

• 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: O-methylmahanine
• 英文别名: 9-methoxy-3,5-dimethyl-3-(4-methylpent-3-enyl)-11H-pyrano[3,2-a]carbazole
• CAS: 38826-51-6
• 化学式: C₂₄H₂₇NO₂
• 分子量: 361.484
• InChiKey: JYCMSEXIUYQQTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3-溴苯氧基)三异丙基硅烷 在 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 copper diacetate 、 palladium diacetate 、 sodium hydride 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 溶剂黄146 、 苯硼酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 146.17h， 生成 O-methylmahanine
  参考文献：
  名称：

  通过硼酸催化的吡喃环环合成7和8加氧的吡喃并[3,2-a]咔唑和吡喃并[2,3-a]咔唑生物碱

  摘要：

  柠檬酸的硼酸催化环化为氧化环化单萜类吡喃咔唑生物碱开辟了一条捷径。因此，从相应的咔唑前体中仅可通过三个步骤获得murrayamine-D，总产率为55％。

  DOI：

  10.1002/chem.201403143

文献信息

• Palladium(<scp>ii</scp>)-catalysed total synthesis of naturally occurring pyrano[3,2-<i>a</i>]carbazole and pyrano[2,3-<i>b</i>]carbazole alkaloids
  作者：Ronny Hesse、Anne Jäger、Arndt W. Schmidt、Hans-Joachim Knölker

  DOI：10.1039/c4ob00367e

  日期：——

  Seven naturally occurring pyranocarbazole alkaloids (pyrayafoline A–E, O-methylmurrayamine A and O-methylmahanine) have been obtained by total synthesis using a palladium(II)-catalysed oxidative cyclisation of a diarylamine to an orthogonally diprotected 2,7-dihydroxycarbazole as key step.

  通过使用钯（II）催化的二芳基胺氧化环化成正交双保护的2,7-二羟基咔唑作为关键化合物，通过全合成获得了七种自然存在的吡喃咔唑生物碱（吡ray啉A–E，O-甲基墨胺A和O-甲基麻红碱）步。
• [EN] SMALL MOLECULE ANDROGEN RECEPTOR INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] PETITES MOLÉCULES INHIBITRICES DU RÉCEPTEUR DES ANDROGÈNES ET PROCÉDÉS D'UTILISATION DE CES DERNIÈRES
  申请人：UNIV GEORGETOWN

  公开号：WO2017023916A1

  公开（公告）日：2017-02-09

  Small molecule carbazole compounds for use as androgen receptor inhibitors are provided herein. Also provided herein are methods for using the carbazole compounds in treating prostate cancer, including castration-resistant prostate cancer and enzalutamide-resistant prostate cancer. The methods include administering to a subject an effective amount of a compound or composition as described herein.

  本文提供了用作雄激素受体抑制剂的小分子咔唑化合物。本文还提供了使用咔唑化合物治疗前列腺癌的方法，包括去势抵抗性前列腺癌和恩扎鲁胺抵抗性前列腺癌的方法。该方法包括向受试者给予本文所述的化合物或组合物的有效量。
• Total Synthesis of 7-Hydroxymurrayazolinine, Murrayamine D, and Mahanine via <i>m</i>-Nitro Group Activated Pyran Annulation
  作者：Shujie Hou、Yong Liu、Yali Kong、Milton L. Brown

  DOI：10.1021/acs.orglett.5b00422

  日期：2015.5.15

  The facile total synthesis of the natural product (±)-mahanine was obtained in eight steps with an overall 52% yield from readily accessible known nitrophenol derivative 6. After a one-step, acid-catalyzed annulation, two additional natural products were formed including 7-hydroxymurrayazolinine, representing its first reported total synthesis. In the whole process, the introduction of the m-nitro

  八步合成天然产物（±）-甘氨酸的简便全合成，从已知的硝基酚衍生物6的总收率达52％。经过一步一步的酸催化环化反应后，形成了另外两个天然产物，包括7-羟基Murrayazolinine，代表了其首次报道的总合成。在整个过程中，在引入的米硝基组显著增强，可通过电感效应的关键吡喃环反应。
• PROCESS FOR THE ISOLATION OF ORGANIC COMPOUNDS USEFUL FOR THE TREATMENT OF CANCER
  申请人：Mandal Chitra

  公开号：US20130065932A1

  公开（公告）日：2013-03-14

  The present invention relates to two main components, mahanine and mahanimbine (dehydroxy-mahanine) from Murraya koenigii for the treatment of glioblastoma and cervical carcinoma. Mahanimbine exhibited anti-cancer activity against lymphoid leukemia, myeloid leukemia, glioma, cervical carcinoma, pancreatic, colon and lung cancers in nineteen cells of different genetic status. C-3 hydroxy and NH groups are responsible contributing groups for their cytotoxicity. Mahanine reduced the doses of cisplatin and paclitaxel in cervical cancer showing better efficacy and useful as an adjunct chemotherapeutic agent to reduce toxicity these two drugs. A new cheap process for this preparation was established. EtOAc extract containing alkaloids enriched with mahanimbine and mahanine, is active against glioma and cervical cancers. Mahanine is targeting the chaperone Hsp90 which led to the proteasome-dependent degradation of several Hsp90-client proteins in diverse carcinoma types, glioblastoma, cervical carcinoma and pancreatic adenocarcinoma irrespective of their tissue origins thereby killing the cancer cells.

  本发明涉及从九里香（Murraya koenigii）中提取的两种主要成分，马哈宁（mahanine）和去羟基马哈宁（mahanimbine），用于治疗胶质母细胞瘤和宫颈癌。去羟基马哈宁在19种不同基因状态的细胞中对淋巴细胞白血病、骨髓性白血病、胶质瘤、宫颈癌、胰腺癌、结肠癌和肺癌等展现出抗癌活性。C-3羟基和NH基团是它们细胞毒性的贡献因子。马哈宁降低了顺铂和紫杉醇在宫颈癌中的剂量，显示出更好的疗效，并可作为辅助化疗药物以减轻这两种药物的毒性。本发明还建立了一种新的廉价制备方法。富含去羟基马哈宁和马哈宁的乙酸乙酯提取物对胶质瘤和宫颈癌具有活性。马哈宁针对分子伴侣蛋白Hsp90，导致多种癌症类型、胶质母细胞瘤、宫颈癌和胰腺腺癌的Hsp90客户蛋白在蛋白酶体依赖性降解下被杀死。
• Small molecule androgen receptor inhibitors and methods of use thereof
  申请人：GEORGETOWN UNIVERSITY

  公开号：US10173978B2

  公开（公告）日：2019-01-08

  Small molecule carbazole compounds for use as androgen receptor inhibitors are provided herein. Also provided herein are methods for using the carbazole compounds in treating prostate cancer, including castration-resistant prostate cancer and enzalutamide-resistant prostate cancer. The methods include administering to a subject an effective amount of a compound or composition as described herein.

  本文提供了用作雄激素受体抑制剂的小分子咔唑化合物。本文还提供了使用咔唑化合物治疗前列腺癌（包括阉割抗性前列腺癌和恩扎鲁胺抗性前列腺癌）的方法。这些方法包括向受试者施用有效量的本文所述化合物或组合物。