2-(trifluoroacetyl)-7,8-(methylenedioxy)-2,3,4,5-tetrahydro-1H-[2]benzazepine-5-spiro-1'-cyclohexa-2',5'-dien-4'-one | 40135-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 2-(trifluoroacetyl)-7,8-(methylenedioxy)-2,3,4,5-tetrahydro-1H-[2]benzazepine-5-spiro-1'-cyclohexa-2',5'-dien-4'-one
• 英文别名: 6'-trifluoroacetyl-5',6',7',8'-tetrahydro-spiro[cyclohexa-2,5-diene-1,9'-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]azepin]-4-one；6-(2,2,2-trifluoroacetyl)spiro[7,8-dihydro-5H-[1,3]dioxolo[4,5-h][2]benzazepine-9,4'-cyclohexa-2,5-diene]-1'-one
• CAS: 40135-91-9
• 化学式: C₁₈H₁₄F₃NO₄
• 分子量: 365.309
• InChiKey: HAWKFAPZXUJREV-UHFFFAOYSA-N

物化性质

• 熔点：
  143-145 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  554.5±50.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(trifluoroacetyl)-7,8-(methylenedioxy)-2,3,4,5-tetrahydro-1H-[2]benzazepine-5-spiro-1'-cyclohexa-2',5'-dien-4'-one 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以90%的产率得到(+/-)-oxocrinine
  参考文献：
  名称：

  5,10b-噻吩啶烷芳科生物碱激发了新型双环系统的发现，该系统具有抗耐药性癌细胞的活性

  摘要：

  石蒜科的植物产生各种各样的生物碱和非碱性次生代谢产物，其中许多因其有希望的抗癌活性而被研究。其中，最近显示基于5,10b-乙基菲啶环系统的可丽宁型生物碱可有效抑制对各种促凋亡刺激具有抵抗力的癌细胞的增殖，并代表对当前化疗难以耐受的肿瘤，例如神经胶质瘤，黑色素瘤，非小细胞肺癌，食道癌，头颈癌等。以这一发现为出发点，并利用简洁的仿生路线通往可丽宁骨架，合成了一系列可丽宁类似物，并针对癌细胞进行了评估。这些化合物表现出一位数的微摩尔活性，并在多种耐药性癌细胞培养物中保留了这种活性。这项研究导致发现了新的双环系统，在开发能够克服癌症化疗耐药性的有效临床抗癌药物中具有巨大潜力。

  DOI：

  10.1016/j.ejmech.2016.05.004
• 作为产物：
  描述：

  6-溴-3,4-亚甲基二氧苯甲醛 在 sodium tetrahydroborate 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 吡啶 为溶剂， 反应 6.5h， 生成 2-(trifluoroacetyl)-7,8-(methylenedioxy)-2,3,4,5-tetrahydro-1H-[2]benzazepine-5-spiro-1'-cyclohexa-2',5'-dien-4'-one
  参考文献：
  名称：

  Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids

  摘要：

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.

  DOI：

  10.1021/jo9807868

文献信息

• METHODS FOR TREATMENT OF RESISTANT CANCER
  申请人：New Mexico Tech Research Foundation

  公开号：US20170313720A1

  公开（公告）日：2017-11-02

  The present disclosure describes a method to treat conditions, including cancer, using compounds that can target resistant cancer cells. The compounds of the invention can decrease the rate of proliferation of drug-resistant cancer cells, such as glioma, lung cancer, and uterine sarcoma.

  本公开描述了一种治疗条件（包括癌症）的方法，使用可以靶向耐药癌细胞的化合物。本发明的化合物可以降低药物耐药癌细胞（如胶质瘤、肺癌和子宫肉瘤）的增殖速率。
• A General Electro‐Synthesis Approach to Amaryllidaceae Alkaloids
  作者：Dennis Pollok、Luca M. Großmann、Torsten Behrendt、Till Opatz、Siegfried R. Waldvogel

  DOI：10.1002/chem.202201523

  日期：2022.9.6

  Highly pharmaceutically relevant Amaryllidaceae alkaloids have been accessed by a versatile electro-organic key transformation, including a precursor of the acetylcholinesterase inhibitor galantamine, used as FDA-approved drug for the treatment of Alzheimer's disease. Spirodienone-type intermediates were obtained in a regioselective and sustainable anodic key transformation from nature-derived starting

  高度药学相关的石蒜科生物碱已通过多功能电有机关键转化获得，其中包括乙酰胆碱酯酶抑制剂加兰他敏的前体，该药物被 FDA 批准用作治疗阿尔茨海默病的药物。螺二烯酮型中间体是通过区域选择性和可持续的阳极关键转化从天然原料中获得的
• Methods for treatment of resistant cancer
  申请人：New Mexico Tech University Research Park Corporation

  公开号：US10414778B2

  公开（公告）日：2019-09-17

  The present disclosure describes a method to treat conditions, including cancer, using compounds that can target resistant cancer cells. The compounds of the invention can decrease the rate of proliferation of drug-resistant cancer cells, such as glioma, lung cancer, and uterine sarcoma.

  本公开内容描述了一种利用可靶向抗药性癌细胞的化合物治疗包括癌症在内的各种疾病的方法。本发明的化合物可以降低抗药性癌细胞的增殖速度，如胶质瘤、肺癌和子宫肉瘤。
• Synthesis of Amaryllidaceae alkaloids, siculine, oxocrinine, epicrinine, and buflavine
  作者：Sumiaki Kodama、Hirofumi Takita、Tetsuya Kajimoto、Kiyoharu Nishide、Manabu Node

  DOI：10.1016/j.tet.2004.03.087

  日期：2004.5

  Three crinane type of alkaloids isolated from Amaryllidaceae family were synthesized by taking advantage of the PIFA-mediated intramolecular p-p' diphenol coupling reaction of norbelladine derivatives. Furthermore, buflavine was also prepared by using the p-p' diphenol coupling followed by dienone-phenol rearrangement as a key step. (C) 2004 Elsevier Ltd. All rights reserved.
• A New H₂O₂/Acid Anhydride System for the Iodoarene-Catalyzed C−C Bond-Forming Reactions of Phenols
  作者：Toshifumi Dohi、Yutaka Minamitsuji、Akinobu Maruyama、Satoshi Hirose、Yasuyuki Kita

  DOI：10.1021/ol801321f

  日期：2008.8.21

  We have succeeded in the first versatile iodoarene-catalyzed C-C bond-forming reactions by development of a new reoxidation system at low temperatures using stoichiometric bis(trifluoroacetyl) peroxide A in 2,2,2-trifluoroethanol (TFE). The catalytic system supplies a wide range of substrates and functional availabilities sufficient to be used in the key synthetic process of producing biologically important Amaryllidaceae alkaloids.