6-Methoxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-Methoxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one
• 英文别名: 6-methoxy-2-(morpholino)chromone；6-Methoxy-2-morpholin-4-ylchromen-4-one
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: VMOFBPPLIBGQRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-乙酰基吗啉 在 三氟甲磺酸酐 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 6-Methoxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  2-氨基色酮的循环脱水途径

  摘要：

  摘要 一系列水杨基乙酰胺与三氟甲磺酸酐的环脱水有效地提供了相应的 2-氨基色酮。在该过程中使用多磷酸酯的效果稍差。

  DOI：

  10.1080/00397919408011307

文献信息

• Carbapenem derivatives containing a bicyclic substituent, process for their preparation, and their use
  申请人：ZENECA LIMITED

  公开号：EP0695753A1

  公开（公告）日：1996-02-07

  The present invention relates to carbapenems and provides a compound of the formula (I) wherein R¹is hydroxymethyl, 1-hydroxyethyl or 1-fluoroethyl; Ris hydrogen or C₁₋₄alkyl; X¹is oxygen or sulphur; and Ais of the formula which is optionally substituted on either ring and wherein B is of the formula -CH₂-C(=O)-(CH₂)n-, -C(=O)-(CH₂)n1-, -C(=O)-CH=CH-X-, -C(=O)CH₂CH₂X-, -(CH₂)nC(=0)NH- or -CH=CHC(=O)NH- wherein n is 1 or 2, n¹ is 2 or 3 and X is NH, 0 or S; and a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof, processes for their preparation, intermediates in their preparation, their use as therapeutic agents and pharmaceutical compositions containing them.

  本发明涉及碳青霉烯，并提供式（I）的化合物，其中R¹是羟甲基，1-羟乙基或1-氟乙基；R是氢或C₁₋₄烷基；X¹是氧或硫；以及A是式的选配取代环上的化合物，其中B是式-CH₂-C（=O）-（CH₂）n-，-C（=O）-（CH₂）n1-，-C（=O）-CH=CH-X-，-C（=O）CH₂CH₂X-，-（CH₂）nC（=0）NH-或-CH=CHC（=O）NH-，其中n为1或2，n¹为2或3，X为NH，0或S；以及其药学上可接受的盐或体内可水解的酯，它们的制备过程，制备中间体，它们作为治疗剂的用途以及含有它们的制药组合物。
• Synthesis and biological evaluation of novel piperazine derivatives of flavone as potent anti-inflammatory and antimicrobial agent
  作者：Girish D. Hatnapure、Ashish P. Keche、Atish H. Rodge、Satish S. Birajdar、Rajesh H. Tale、Vandana M. Kamble

  DOI：10.1016/j.bmcl.2012.08.071

  日期：2012.10

  A series of novel 6-methoxy-2-(piperazin-1-yl)-4H-chromen-4-one and 5,7-dimethoxy-2-(piperazin-1-ylmethyl)-4H-chromen-4-one derivatives of biological interest were prepared and screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Among all the compound screened (5a-j and 10k-t), the compounds 5c, 5g, 5h, 10l, 10m, 10n and 10r found to have promising anti-inflammatory activity (up to 65-87% TNF-alpha and 70-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (71% TNF-a and 84% IL-6 inhibitory activities at 1 mu M) while the compounds5b, 5i, 5j, 10s and 10t found to be potent antimicrobial agent showing even 2 to 2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL. (c) 2012 Elsevier Ltd. All rights reserved.
• Syntheses and Evaluation of 2- or 3-(<i>N</i>-Cyclicamino)chromone Derivatives as Monoamine Oxidase Inhibitors
  作者：Koichi Takao、Tsukasa Sakatsume、Hitoshi Kamauchi、Yoshiaki Sugita

  DOI：10.1248/cpb.c20-00579

  日期：2020.11.1

  A series of 2-(N-cyclicamino)chromone derivatives (1a-4c) and 3-(N-cyclicamino)chromone derivatives (5a-8c) were synthesized, and their monoamine oxidase (MAO) A and B inhibitory activities were studied as part of a structure-activity relationship investigation. Compounds 1a-4c showed no remarkable inhibition for MAO-A or MAO-B, whereas compounds 5a-8c (with a few exceptions) showed significant and selective inhibition of MAO-B. Of these compounds, 7c,7-methoxy-3-(4-phenyl-1-piperazinyl)-4H-1-benzopyran-4-one inhibited MAO-B the most potently and selectively, having IC50 of 15 nM and an MAO-B selectivity index of more than 6700; c.f, 50 nM and 2000, respectively, for safinamide. The mode of inhibition of 7c to MAO-B was competitive and reversible. Considering the IC50 values and selectivity indices of the other synthetic compounds, the presence of the methoxy group on the chromone ring (R-2) of 7c seemed to increase MAO-B inhibition. Molecular docking analysis also supports this hypothesis. Our results suggest that 3-(N-cyclicamino)chromones are useful lead compounds for the development of MAO-B inhibitors.
• ANTIATHEROSCLEROTIC AND ANTITHROMBOTIC 1-BENZOPYRAN-4-ONES AND 2-AMINO-1,3-BENZOXAZINE-4-ONES
  申请人：THE UPJOHN COMPANY

  公开号：EP0459983A1

  公开（公告）日：1991-12-11
• US5607928A
  申请人：——

  公开号：US5607928A

  公开（公告）日：1997-03-04