1-(6-甲氧基-2H-色烯-3-基)-1-乙酮 | 57543-56-3

• 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: 1-(6-甲氧基-2H-色烯-3-基)-1-乙酮
• 英文名称: 1-(6-methoxy-2H-chromen-3-yl)ethanone
• 英文别名: 3-acetyl-6-methoxy-2H-chromene；3-acetyl-6-methoxy-2H-chromen；1-(6-methoxy-2H-chromen-3-yl)-ethanone；6-methoxy-3-acetyl-2H-chromene；3-Acetyl-6-methoxy-Δ³-chromen；2H-1-Benzopyran, 3-acetyl-6-methoxy-
• CAS: 57543-56-3
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: BEOYIJRGYVVEHY-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

安全信息

• 安全说明：
  SModerately
• 储存条件：
  库房应保持通风、低温和干燥的环境。

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

• 作为反应物：
  描述：

  1-(6-甲氧基-2H-色烯-3-基)-1-乙酮 在 碳酸氢钠 、 copper(ll) bromide 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 3-[2-(3-hydroxycarbonyl)phenylaminoacetyl]-6-methoxy-2H-chromen-2-one
  参考文献：
  名称：

  Identification of novel molecular scaffolds for the design of MMP-13 inhibitors: A first round of lead optimization

  摘要：

  Osteoarthritis (OA) is the leading cause of joint pain and disability in middle-aged and elderly patients, and is characterized by progressive loss of articular cartilage. Among the various matrix metalloproteinases (MMPs), MMP-13 is specifically expressed in the cartilage of human OA patients and is not present in normal adult cartilage. Thus. MMP-13-selective inhibitors are promising candidates in ostearthritis therapy. Recently, we designed an N-isopropoxy-arylsulfonamide-based hydroxamate inhibitor, which showed low nanomolar activity and high selectivity for MMP-13. In parallel to further studies aiming to assess the in vivo activity of our compound, we screened the Life Chemicals database through computational docking to seek for novel scaffolds as zinc-chelating non-hydroxamate inhibitors. Experimental evaluation of 20 selected candidate compounds verified five novel leads with IC50 in the low mu M range. These newly discovered inhibitors are structurally unrelated to the ones known so far and provide useful scaffolds to develop compounds with more desirable properties. Finally, a first round of structure-based optimization on lead 1 was accomplished and led to an increase in potency of more than 5 fold. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.035
• 作为产物：
  描述：

  4-甲氧基苯酚 在 potassium carbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 生成 1-(6-甲氧基-2H-色烯-3-基)-1-乙酮
  参考文献：
  名称：

  Chromene-Based Synthetic Chalcones as Potent Antileishmanial Agents: Synthesis and Biological Activity

  摘要：

  Two types of regioisomeric chromene‐based chalcones namely, 1‐(6‐methoxy‐2H‐chromen‐3‐yl)‐3‐phenylpropen‐1‐ones and 3‐(6‐methoxy‐2H‐chromen‐3‐yl)‐1‐phenylpropen‐1‐ones were prepared and investigated for their antileishmanial activity against promastigotes form of Leishmania major. The obtained results from in vitro biological assays indicated that chloro‐substituted 1‐(6‐methoxy‐2H‐chromen‐3‐yl)‐3‐phenylpropen‐1‐ones exhibited excellent activity against Leishmania major at non‐cytotoxic concentrations.

  DOI：

  10.1111/j.1747-0285.2010.00959.x

文献信息

• Cytotoxic activity evaluation and QSAR study of chromene-based chalcones
  作者：Loghman Firoozpour、Najmeh Edraki、Maryam Nakhjiri、Saeed Emami、Maliheh Safavi、Sussan Kabudanian Ardestani、Mehdi Khoshneviszadeh、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1007/s12272-012-1208-2

  日期：2012.12

  Chalcone and chromene motifs are synthetic or naturally occurring scaffolds with significant cytotoxic profile. Two types of novel regioisomeric chromene-chalcone hybrids, namely 1-(6-chloro or 6-methoxy-2H-chromen-3-yl)-3-phenylprop-2-en-1-one (Type A) and 3-(6-chloro or 6-methoxy-2H-chromen-3-yl)-1-phenylprop-2-en-1-one (Type B), both with different substituents on the phenyl ring attached to propenone linkage, have been evaluated for their cytotoxic activity against breast cancer cell lines (MCF-7 and MDA-MB-231). The results indicate that type A of chromene-chalcones demonstrated better cytotoxic profile than type B especially in MDA-MB-231 cell line. In addition, the growth inhibitory activity of most of the target compounds is higher than Etoposide as a reference drug. QSAR analysis of these novel compounds demonstrated that topological and geometrical parameters are among the important descriptors that influence the cytotoxic activity profile of compounds.

  查尔克酮和色烯基是合成或天然存在的框架，具有显著的细胞毒性特征。两种新型区域异构体色烯-查尔克酮杂交物，即1-(6-氯或6-甲氧基-2H-色烯-3-基)-3-苯基丙-2-烯-1-酮（类型A）和3-(6-氯或6-甲氧基-2H-色烯-3-基)-1-苯基丙-2-烯-1-酮（类型B），两者在连接端的苯环上具有不同的取代基，已被评估其对乳腺癌细胞系（MCF-7和MDA-MB-231）的细胞毒性活性。结果表明，类型A的色烯-查尔克酮在MDA-MB-231细胞系中表现出比类型B更好的细胞毒性特征。此外，大多数目标化合物的生长抑制活性高于作为参考药物的依托泊苷。对这些新化合物的QSAR分析表明，拓扑和几何参数是影响化合物细胞毒性活性特征的重要描述符之一。
• ¹ H and ¹³ C NMR spectral assignments of novel chromenylchalcones
  作者：Hyuk Yoon、Seunghyun Ahn、Doseok Hwang、Geunhyeong Jo、Dong Woon Kim、Sang Ho Kim、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.3873

  日期：2012.11

  were also synthesized through the same reaction between aldehydes (I) and ketone (II). Their complete 1H‐NMR and 13C‐NMR assignments are reported here and more polysubstituted chromenylchalcones synthesized or isolated from the natural sources in the future can be identified on the basis of the NMR data reported here. Copyright © 2012 John Wiley & Sons, Ltd.

  合成了几种含有 2H-色烯基团的查耳酮。2H-chromen-3-甲醛 (I) 与甲氧基取代的苯乙酮的 Claisen-Schmidt 缩合得到 (E)-3-(2H-chromen-3-yl)-1-(甲氧基苯基)prop-2-en-1-ones （色基查耳酮，1-7）。其他类型的色烯基查尔酮 (E)-1-(6-甲氧基-2H-色烯-3-基)-3-(甲氧基苯基)丙-2-烯-1-酮 (8-13)甲氧基取代的苯甲醛和 1-(6-甲氧基-2H-色烯-3-基)乙酮 (II)。Dichromenychalcones (14-16) 也通过醛 (I) 和酮 (II) 之间的相同反应合成。此处报告了它们完整的 1H-NMR 和 13C-NMR 归属，未来可以根据此处报告的 NMR 数据确定更多合成或从天然来源中分离的多取代的色基查耳酮。
• 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。
• 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.
• Catalytical promiscuity of α-amylase: Synthesis of 3-substituted 2H-chromene derivatives via biocatalytic domino oxa-Michael/aldol condensations
  作者：Long-Hua Zhou、Na Wang、Wei Zhang、Zong-Bo Xie、Xiao-Qi Yu

  DOI：10.1016/j.molcatb.2013.02.001

  日期：2013.7

  An facile and green one-pot route has been developed for the synthesis of chromenes using salicylaldehyde and alpha,beta-unsaturated ketones. alpha-Amylase from Bacillus subtilis shows excellent catalytic activity and exerts good adaptability to different substrates in the reaction. This promiscuous enzyme-catalyzed domino reaction not only extends the application of alpha-amylase from B. subtilis for new chemical transformations, but also provided an alternative synthetic method for 2H-chromene derivatives. (c) 2013 Elsevier B.V. All rights reserved.