3-乙酰基-7-甲氧基-2H-1-苯并吡喃 | 57543-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 3-乙酰基-7-甲氧基-2H-1-苯并吡喃
• 英文名称: 1-(7-methoxy-2H-chromen-3-yl)ethanone
• 英文别名: 2H-1-Benzopyran, 3-acetyl-7-methoxy-
• CAS: 57543-55-2
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: IXPOUIHJJIXKFS-UHFFFAOYSA-N

物化性质

• 沸点：
  302.71°C (rough estimate)
• 密度：
  1.1554 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

制备方法与用途

类别：易燃液体
毒性分级：中毒
急性毒性：腹腔-小鼠 LD50: 1000 毫克/公斤
可燃性危险特性：可燃；加热分解时释放刺激烟雾
储运特性：库房通风、低温干燥
灭火剂：干粉、泡沫、砂土、二氧化碳、雾状水

反应信息

• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 丁烯酮 在 吡啶 、 sodium hydroxide 、 potassium carbonate 作用下， 以 N-甲基乙酰胺 为溶剂， 以42%的产率得到3-乙酰基-7-甲氧基-2H-1-苯并吡喃
  参考文献：
  名称：

  New heteroarotinoid compounds

  摘要：

  通式（I）的化合物：##STR1##其中：R表示氢原子、卤原子或羟基、低烷基、低烷氧基、羧基、（低烷氧基）羰基、（低芳基烷氧基）羰基、氨基羰基、（低烷基或双烷基）氨基羰基或（低芳基烷基）氨基羰基、带有杂环基团的N-取代氨基羰基，或硫基、（低烷基）硫基、磺酰基或（低烷基）磺酰基，R.sub.1、R.sub.2、R.sub.3和R.sub.4，可能相同也可能不同，表示氢原子、卤原子或低烷基、低烯基、低烷氧基或低烯氧基，可选地取代一个或多个卤原子，它们的异构体、对映体、非对映体异构体，以及当R表示羧基时，它们与药学上可接受的碱形成的加合盐，以及当R含有碱性基团时，它们与药学上可接受的酸形成的加合盐。

  公开号：

  US04975455A1

文献信息

• New heteroarotinoid compounds
  申请人：Adir et Cie

  公开号：US04975455A1

  公开（公告）日：1990-12-04

  Compounds of general formula (I): ##STR1## in which: R denotes a hydrogen atom, a halogen atom or a hydroxy, lower alkyl, lower alkyloxy, carboxyl, (lower alkyloxy)carbonyl, (lower arylalkyloxy)carbonyl, aminocarbonyl, (lower mono- or dialkyl)aminocarbonyl or (lower arylalkyl)aminocarbonyl group, an aminocarbonyl group N-substituted with a heterocyclic radical, or a thio, (lower alkyl)thio, sulfonyl or (lower alkyl)sulfonyl group, R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote a hydrogen atom, a halogen atom or a lower alkyl, lower alkenyl, lower alkyloxy or lower alkenyloxy group, optionally substituted with one or more halogen atoms, their isomers, enantiomers, diastereoisomers and also, when R denotes a carboxyl, their addition salts with a pharmaceutically acceptable base and, when R contains a basic group, their addition salts with a pharmaceutically acceptable acid.

  通式（I）的化合物：##STR1##其中：R表示氢原子、卤原子或羟基、低烷基、低烷氧基、羧基、（低烷氧基）羰基、（低芳基烷氧基）羰基、氨基羰基、（低烷基或双烷基）氨基羰基或（低芳基烷基）氨基羰基、带有杂环基团的N-取代氨基羰基，或硫基、（低烷基）硫基、磺酰基或（低烷基）磺酰基，R.sub.1、R.sub.2、R.sub.3和R.sub.4，可能相同也可能不同，表示氢原子、卤原子或低烷基、低烯基、低烷氧基或低烯氧基，可选地取代一个或多个卤原子，它们的异构体、对映体、非对映体异构体，以及当R表示羧基时，它们与药学上可接受的碱形成的加合盐，以及当R含有碱性基团时，它们与药学上可接受的酸形成的加合盐。
• BRION, JEAN-DANIEL;LE, BAUT GUILLAUME;DUCREY, PATRICK;PIESSARD-ROBERT, SY+
  作者：BRION, JEAN-DANIEL、LE, BAUT GUILLAUME、DUCREY, PATRICK、PIESSARD-ROBERT, SY+

  DOI：——

  日期：——
• US4975455A
  申请人：——

  公开号：US4975455A

  公开（公告）日：1990-12-04
• Polyphenols bearing cinnamaldehyde scaffold showing cell growth inhibitory effects on the cisplatin-resistant A2780/Cis ovarian cancer cells
  作者：Soon Young Shin、Hyeryoung Jung、Seunghyun Ahn、Doseok Hwang、Hyuk Yoon、Jiye Hyun、Yeonjoong Yong、Hi Jae Cho、Dongsoo Koh、Young Han Lee、Yoongho Lim

  DOI：10.1016/j.bmc.2014.01.058

  日期：2014.3

  Ovarian carcinoma remains the most lethal among gynecological cancers. Chemoresistance is a clinical problem that severely limits treatment success. To identify potent anticancer agents against the cisplatin-resistant human ovarian cancer cell line A2780/Cis, 26 polyphenols bearing a cinnamaldehyde scaffold were synthesized. Structural differences in their inhibitory effect on clonogenicity of A2780/Cis cells were elucidated using comparative molecular field analysis and comparative molecular similarity indices analysis. Structural conditions required for increased inhibitory activity can be derived based on the analysis of their contour maps. The two most active compounds (16 and 19) were selected and further characterized their biological activities. We found that compounds 16 and 19 trigger cell cycle arrest at the G2/M phase and apoptotic cell death in cisplatin-resistant A2780/Cis human ovarian cancer cells. The molecular mechanism of compound 16 was elucidated using in vitro aurora A kinase assay, and the binding mode between the compound 16 and aurora A kinase was interpreted using in silico docking experiments. The findings obtained here may help us develop novel plant-derived polyphenols used for potent chemotherapeutic agents. In conclusion, compounds 16 and 19 could be used as promising lead compounds for the development of novel anticancer therapies in the treatment of cisplatin-resistant ovarian cancers. (C) 2014 Elsevier Ltd. All rights reserved.