(4-fluoro-phenyl)-(5-methoxy-1H-indol-2-yl)-methanone

• 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: (4-fluoro-phenyl)-(5-methoxy-1H-indol-2-yl)-methanone
• 英文别名: 4-fluorophenyl(5-methoxy-1H-2-indolyl)-1-methanone；(4-fluorophenyl)-(5-methoxy-1H-indol-2-yl)methanone
• 化学式: C₁₆H₁₂FNO₂
• 分子量: 269.275
• InChiKey: HJRVZFSFLCZANJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(苯磺酰基)-5-甲氧基吲哚 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.5h， 生成 (4-fluoro-phenyl)-(5-methoxy-1H-indol-2-yl)-methanone
  参考文献：
  名称：

  Synthetic 2-Aroylindole Derivatives as a New Class of Potent Tubulin-Inhibitory, Antimitotic Agents

  摘要：

  A new class of simple synthetic antimitotic compounds based on 2-aroylindoles was discovered. (5-Methoxy-1H-2-indolyl)-phenylmethanone (1) as well as analogous 3-fluorophenyl- (36) and 3-methoxyphenyl (3) derivatives displayed high cytotoxicity Of IC50 = 20 to 75 nM against the human HeLa/KB cervical, SK-OV-3 ovarian, and U373 astrocytoma carcinoma cell lines. The inhibition of proliferation correlated with the arrest in the G2/M phase of the cell cycle. In in vitro assays with tubulin isolated from bovine brain, in general antiproliferative activity correlated with inhibition of tubulin polymerization. Thus, the antimitotic activity of 2-aroylindoles is explained by interference with the mitotic spindle apparatus and destabilization of microtubules. In contrast to colchicine, vincristine, nocodazole, or taxol, I did not significantly affect the GTPase activity of beta -tubulin. Interestingly, selected compounds inhibited angiogenesis in the chorioallantoic membrane (CAM) assay. In xenograft experiments, 1 was highly active after oral administration at 200 mg/kg against the human amelanocytic melanoma MEXF 989 in athymic nude mice. We conclude, that 2-aroylindoles constitute an interesting new class of antitubulin agents with the potential to be clinically developed for cancer treatment.

  DOI：

  10.1021/jm010940+

文献信息

• Cyclic and acyclic propenones for treating CNS disorders
  申请人：Kalvinsh Ivars

  公开号：US20060074083A1

  公开（公告）日：2006-04-06

  The invention relates to novel cyclic and non-cyclic propenone derivatives as well as their pharmaceutically acceptable slats. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are useful as medicaments.

  该发明涉及新颖的环状和非环状丙烯酮衍生物以及它们的药用可接受盐。该发明还涉及一种制备这类化合物的方法。该发明的化合物可用作药物。
• 2-acyl indole derivatives and their use as antitumor agents
  申请人：——

  公开号：US20020091124A1

  公开（公告）日：2002-07-11

  The invention relates to novel indole and heteroindole derivatives of the formula I 1 to their tautomers, their stereoisomers, their mixtures and their salts, to their preparation and to the use of indole derivatives of the formula I as antitumor agents.

  这项发明涉及到式I的新型吲哚和杂吲哚衍生物，以及它们的互变异构体、立体异构体、混合物和盐，以及它们的制备和将式I的吲哚衍生物用作抗肿瘤药剂。
• Formic Acid as Carbon Monoxide Source in the Palladium-Catalyzed N-Heterocyclization of <i>o</i>-Nitrostyrenes to Indoles
  作者：Manar Ahmed Fouad、Francesco Ferretti、Fabio Ragaini

  DOI：10.1021/acs.joc.2c02613

  日期：——

  generation of CO from nontoxic and affordable sources. Among several CO sources that have been previously explored for the generation of gaseous CO, here we report the use of cheap and readily available formic acid as an effective reductant for the reductive cyclization of o-nitrostyrenes. The reaction is air and water tolerant and provides the desired indoles in yields up to 99%, at a low catalyst loading

  使用 CO 作为廉价还原剂，研究了邻硝基苯乙烯生成吲哚的还原环化反应已有 30 年，但它仍然是一个有趣的研究和改进领域。然而，使用有毒的 CO 气体有几个缺点。因此，非常优选使用安全有效的替代品从无毒且负担得起的来源原位生成 CO。在先前探索用于产生气态 CO 的几种 CO 来源中，我们在此报告使用廉价且容易获得的甲酸作为有效还原剂，用于还原环化o-硝基苯乙烯。该反应具有空气和水耐受性，并以高达 99% 的收率提供所需的吲哚，催化剂负载量较低 (0.5 mol%)，并且不会产生有毒或难以分离的副产物。可以使用便宜的玻璃厚壁“压力管”代替较少可用的高压灭菌器，即使在 2 g 的规模上，从而扩大了我们协议的适用性。
• NOVEL CYCLIC AND ACYCLIC PROPENONES FOR TREATING CNS DISORDERS
  申请人：Merz Pharma GmbH & Co.KGaA

  公开号：EP1804781A1

  公开（公告）日：2007-07-11
• [EN] NOVEL CYCLIC AND ACYCLIC PROPENONES FOR TREATING CNS DISORDERS<br/>[FR] NOUVELLES PROPENONES CYCLIQUES ET ACYCLIQUES DESTINEES AU TRAITEMENT DES TROUBLES DU SNC
  申请人：MERZ PHARMA GMBH & CO KGAA

  公开号：WO2006037996A1

  公开（公告）日：2006-04-13

  The invention relates to novel cyclic and non-cyclic propenone derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are useful as medicaments.