2-amino-4-(3-methoxy-4-hydroxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile | 315245-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-amino-4-(3-methoxy-4-hydroxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-4-(4-hydroxy-3-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-4-(4-hydroxy-3-methoxyphenyl)-5-oxo-4,6,7,8-tetrahydrochromene-3-carbonitrile
• CAS: 315245-09-1
• 化学式: C₁₇H₁₆N₂O₄
• 分子量: 312.325
• InChiKey: CYUCOXMWXGGJJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-4-(3-methoxy-4-hydroxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 在 溶剂黄146 作用下， 生成 4-(4-methoxyaniline)-5-(4-hydroxy-3-methoxyphenyl)-8,9-dihydro-5H-chromeno[2,3-d]pyrimidin-6(7H)-one
  参考文献：
  名称：

  作为黄嘌呤氧化酶抑制剂的稠合吡喃并[3,2-d]嘧啶衍生物的合成，筛选和对接。

  摘要：

  鉴于开发有效的黄嘌呤氧化酶（XO）酶抑制剂，合成了一系列100种吡喃并[3,2-d]嘧啶衍生物，并对其体外XO酶抑制进行了评估。结构活动关系也已建立。在所有合成的化合物中，发现4d，8d和9d是最有效的酶抑制剂，IC50值分别为8μM，8.5μM和7μM。在酶动力学研究中进一步研究了化合物9d，Lineweaver-Burk图显示化合物9d是混合型抑制剂。还已经计算出最有效的化合物4d，8d和9d的分子性质。进行了对接研究以研究黄嘌呤氧化酶与最有效的XO抑制剂9d之间的识别模式。

  DOI：

  10.1016/j.ejmech.2017.03.002
• 作为产物：
  描述：

  1,3-环己二酮 、 香草醛 、 丙二腈 在 benzyl ((4-fluorophenyl)carbamoyl)-L-leucyl-L-phenylalaninate 、 cytochrome c 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.5h， 以88%的产率得到2-amino-4-(3-methoxy-4-hydroxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  A cytochrome c-urea functionalized dipeptide conjugate: an efficient HBD framework to synthesize 4H-pyrans via one-pot multicomponent reaction

  摘要：

  这项工作专注于开发一个高效且环保的一锅多组分合成协议，用于合成一系列4H-吡喃衍生物。

  DOI：

  10.1039/c9gc03512e

文献信息

• Synthesis, molecular modeling and BACE-1 inhibitory study of tetrahydrobenzo[b] pyran derivatives
  作者：Vijaya Bhaskar、Reshma Chowdary、Sheshagiri R. Dixit、Shrinivas D. Joshi

  DOI：10.1016/j.bioorg.2018.11.023

  日期：2019.3

  documented as one of the possible therapeutic targets for the treatment of Alzheimer's disease. In this paper, we report the synthesis and the for β-secretase (BACE-1) inhibitory activity of new series of tetrahydrobenzo [b] pyran derivatives. One-pot synthesis of tetrahydrobenzo [b] pyrans was carried out by condensing aromatic aldehyde, malononitrile and 1,3-cyclohexanedione using ionic liquid 1-butyl-3-methyl

  β-分泌酶（BACE1）已被广泛证明是治疗阿尔茨海默氏病的可能治疗靶标之一。在本文中，我们报告了新系列的四氢苯并[b]吡喃衍生物的合成及其对β-分泌酶（BACE-1）的抑制活性。一锅法合成四氢苯并[b]吡喃是通过在水性醇介质中使用离子液体1-丁基-3-甲基咪唑鎓氯化物（[bmIm] Cl-）缩合芳族醛，丙二腈和1,3-环己二酮来进行的。乙醇和水的比例为1：2，可使所有反应物保持在溶液中，这有助于反应并非常容易地形成产物。对合成的化合物进行BACE1抑制分析，六个化合物4d，4e，4f，4h，4i和4p在微摩尔水平显示出显着的IC50值。在这六种活性化合物中，4e是一种潜在的抑制剂，其IC50值在纳摩尔范围内。所有合成的化合物都停靠在β-分泌酶的活性位点上。
• One-pot cascade synthesis of benzopyrans and dihydropyrano[c]chromenes catalyzed by lipase TLIM
  作者：Yajie Fu、Zeping Lu、Xiaolong Ma、Ke Fang、Xinyi He、Huajin Xu、Yi Hu

  DOI：10.1016/j.bioorg.2020.103888

  日期：2020.6

  Lipase TLIM was reported to be an efficient, commercially available and reusable catalyst for the Knoevenagel-Michael cascade reactions of aldehydes, malononitrile/ethyl cyanoacetate and 4-hydroxycoumarin/1, 3-cyclohexanedione/dimedone in aqueous DMSO. This methodology presents many superiorities such as simple procedure, mild reaction conditions, commercially available and reusable catalyst, high

  据报道，脂肪酶TLIM是在DMSO水溶液中的醛，丙二腈/氰基乙酸乙酯和4-羟基香豆素/ 1、3-环己烷二酮/二甲酮的Knoevenagel-Michael级联反应的有效，可商购且可重复使用的催化剂。该方法学具有许多优点，例如操作简单，反应条件温和，可商购和可重复使用的催化剂，高底物适用性，按比例放大的能力以及良好的优异收率。
• Brønsted acidic ionic liquid catalyzed highly efficient synthesis of chromeno pyrimidinone derivatives and their antimicrobial activity
  作者：Janardhan Banothu、Rajitha Bavanthula

  DOI：10.1016/j.cclet.2012.06.041

  日期：2012.9

  honium hydrogen sulfate as catalyst. Structures of all the compounds were established on the basis of analytical and spectroscopic data. All the compounds were evaluated for their in vitro antimicrobial activity against different bacterial and fungal strains.

  一系列的8,9-二氢-2-（2-oxo-2 H -chromen-3-yl）-5-aryl-3 H -chromeno [2,3 - d ]嘧啶-4,6（5 H， 7 H）-二酮（5a-j）是通过2-氨基-5,6,7,8-四氢-5-氧代-4-芳基-4 H-色烯-3-腈（4a – j）在纯条件下，用布朗斯台德酸性离子液体（4-磺丁基）三（4-磺苯基）phosph硫酸氢盐作催化剂，用香豆素-3-羧酸进行催化。所有化合物的结构都是根据分析和光谱数据确定的。对所有化合物进行了体外评估 对不同细菌和真菌菌株的抗菌活性。
• Screening of a library of 4-aryl/heteroaryl-4H-fused pyrans for xanthine oxidase inhibition: synthesis, biological evaluation and docking studies
  作者：Ramandeep Kaur、Fatima Naaz、Sahil Sharma、Samir Mehndiratta、Manish Kumar Gupta、Preet Mohinder Singh Bedi、Kunal Nepali

  DOI：10.1007/s00044-015-1382-0

  日期：2015.8

  A series of 4-aryl/heteroaryl-4H-fused pyrans was synthesized via multicomponent reaction in a microwave synthesizer. All the pyrans were evaluated for in vitro xanthine oxidase inhibition. Structure-activity relationship was also established. Among the series of 108 compounds, Compound 5n was the most potent displaying remarkable inhibition against the enzyme with an IC50 value of 0.59 mu M. Enzyme kinetic study was carried out for the compound 5n to determine the type of inhibition. The study revealed that the compound 5n was a mixed-type inhibitor. Molecular modelling studies were also performed to figure out the interactions of both the enantiomers of 5n with the amino acid residues of the enzyme.[GRAPHICS].
• Synthesis of biscoumarin and dihydropyran derivatives with promising antitumor and antibacterial activities
  作者：Jing Li、Yun-Peng Sui、Jia-Jia Xin、Xin-Liang Du、Jiang-Tao Li、Hai-Ru Huo、Hai Ma、Wei-Hao Wang、Hai-Yu Zhou、Hong-Dan Zhan、Zhu-Ju Wang、Chun Li、Feng Sui、Xia Li

  DOI：10.1016/j.bmcl.2015.10.063

  日期：2015.12

  Two series of biscoumarin (1-3) and dihydropyran (4-12) derivatives were successfully synthesized as new antitumor and antibacterial agents. The molecular structures of four representative compounds 2, 4, 7 and 10 were confirmed by single crystal X-ray diffraction study. The synthesized compounds (1-12) were evaluated for their antitumor activities against human intestinal epithelial adenocarcinoma cell line (HuTu80), mammary adenocarcinoma cell line (4T1) and pancreatic cancer cell line (PANC1) and antibacterial activities against one drug-sensitive Staphylococcus aureus (S. aureus ATCC 29213) strain and three MRSA strains (MRSA XJ 75302, Mu50, USA 300 LAC). The further mechanism study demonstrated that the most potent compound 1 could obviously inhibit the proliferation of cancer cells via the mechanism to induce apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.