2-amino-4-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-4-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-5,6,7,8-tetrahydro-4-(napthalen-1-yl)-5-oxo-4H-chromene-3-carbonitrile；2-amino-6,6,7,7,8,8-hexahydro-5-oxo-4-(1-naphthyl)-4H-chromene-3-carbonitrile；2-amino-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-4-naphthalen-1-yl-5-oxo-4,6,7,8-tetrahydrochromene-3-carbonitrile
• 化学式: C₂₀H₁₆N₂O₂
• 分子量: 316.359
• InChiKey: FHUZCSSBSXJQNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-(naphthalen-1-yl)-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-(naphthyl)-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：

  2-(萘-1-基亚甲基)丙二腈 、 1,3-环己二酮 在 吗啉 作用下， 以 乙醇 为溶剂， 以95%的产率得到2-amino-4-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  2-Amino-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile and 2-amino-7,7-dimethyl-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

  摘要：

  Syntheses and X-ray structural investigations have been carried out for the two title compounds, C20H16N2O2, (IIIa), and C22H20N2O2, (IIIb). In (IIIa), the heterocyclic ring adopts a sofa conformation, while in (IIIb), the ring has a flattened boat conformation. In both molecules, the fused cyclohexenone ring adopts a sofa conformation. The dihedral angles between these two at fragments are 3.5 (2) and 17.5 (2)degrees in (IIIa) and (IIIb), respectively. The dihedral angles between the pseudo-axial naphthalene substituents and the planes of the pyran rings are 90.9 (1) and 96.7 (1)degrees, respectively. In the crystal structure of (IIIa), intermolecular N-H...N and N-H...O hydrogen bonds link the molecules into infinite tapes along the b axis, while molecules of (IIIb) form centrosymmetric dimers via N-H...N hydrogen bonds, with only one H atom of the NH2 donor group taking part in hydrogen bonding.

  DOI：

  10.1107/s0108270104006924

文献信息

• A cytochrome c-urea functionalized dipeptide conjugate: an efficient HBD framework to synthesize 4<i>H</i>-pyrans <i>via</i> one-pot multicomponent reaction
  作者：Sanjeev Saini、Mayank、Navneet Kaur、Narinder Singh

  DOI：10.1039/c9gc03512e

  日期：——

  This work is focused on the development of an efficient and green protocol for the one-pot multicomponent synthesis of a series of 4H-pyran derivatives.

  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。
• Effect of Substituents on the Crystal Structures, Optical Properties, and Catalytic Activity of Homoleptic Zn(II) and Cd(II) β-oxodithioester Complexes
  作者：Chote Lal Yadav、Anamika、Gunjan Rajput、Kamlesh Kumar、Michael G. B. Drew、Nanhai Singh

  DOI：10.1021/acs.inorgchem.0c01195

  日期：2020.8.17

  Five novel zinc(II) and cadmium(II) β-oxodithioester complexes, [Zn(L1)2] (1), [Zn(L2)2]n (2), [Zn(L3)2]n (3) [Cd(L1)2]n (4), [Cd(L2)2]n (5), with β-oxodithioester ligands, where L1 = 3-(methylthio)-1-(thiophen-2-yl)-3-thioxoprop-1-en-1-olate, L2 = 3-(methylthio)-1-(pyridin-3-yl)-3-thioxoprop-1-en-1-olate, and L3 = 3-(methylthio)-1-(pyridin-4-yl)-3-thioxoprop-1-en-1-olate, were synthesized and characterized

  五个新颖的锌（II）和镉（II）β-氧二硫酯配合物[Zn（L1）2 ]（1），[Zn（L2）2 ] n（2），[Zn（L3）2 ] n（3） [Cd（L1）2 ] n（4），[Cd（L2）2 ] n（5），具有β-氧二硫酯配体，其中L1 = 3-（甲硫基）-1-（噻吩-2-基）-3 -thioxoprop-1-en-1-olate，L2= 3-（甲硫基）-1-（吡啶-3-基）-3-硫代丙-1--1-烯酸酯，L3 = 3-（甲硫基）-1-（吡啶-4-基）-3-合成并通过元素分析，IR，UV-vis和NMR光谱（1 H和13 C 1 H}）对thioxoprop-1-en-1-olate进行了表征。所有配合物的固态结构通过单晶X射线晶体学确定。的β-oxodithioester配体键合至的Zn（II）/镉（II）中的O的金属离子∧ S和N的螯合剂/螯合剂桥接方式导致1D的形成（在2 - 4
• Mn(III)-pentadentate Schiff base complex supported on multi-walled carbon nanotubes as a green, mild and heterogeneous catalyst for the synthesis of tetrahydrobenzo[<i>b</i> ]pyrans via tandem Knoevenagel-Michael cyclocondensation reaction
  作者：Jamshid Rakhtshah、Sadegh Salehzadeh、Mohammad Ali Zolfigol、Saeed Baghery

  DOI：10.1002/aoc.3690

  日期：2017.9

  coupled plasma mass spectrometry, elemental analysis and thermogravimetric analysis. A facile, eco‐friendly, mild and green procedure was developed for the one‐pot three‐component synthesis of tetrahydrobenzo[b]pyrans via tandem Knoevenagel–Michael cyclocondensation reactions between aromatic aldehydes, 1,3‐diones and malononitrile using a catalytic amount of Mn(III)–pentadentate Schiff base complex

  设计并使用红外光谱，X射线衍射，扫描电子显微镜，能量色散X设计并支撑了多壁碳纳米管上负载的Mn（III）-五齿Schiff碱配合物，作为可回收和可重复使用的绿色和纳米多相催化剂。射线光谱法，电感耦合等离子体质谱法，元素分析和热重分析。开发了一种简便，环保，温和且绿色的程序，用于一锅三组分合成四氢苯并[ b]芳醛，1,3-二酮和丙二腈之间的串联Knoevenagel–Michael环缩合反应生成吡喃，使用催化量的Mn（III）-五齿Schiff碱配合物在MWCNTs上作为无溶剂条件下的有效可回收多相催化剂在室温下使用温度。该工艺的优点是易于获得，稳定，可回收利用和催化剂的环保性，反应时间短，产率高至优异以及后处理程序简单。
• Practical and Green Protocol for the Synthesis of Substituted 4<i>H</i>-Chromenes Using Room Temperature Ionic Liquid Choline Chloride-Urea
  作者：C. N. Revanna、T. R. Swaroop、G. M. Raghavendra、D. G. Bhadregowda、K. Mantelingu、K. S. Rangappa

  DOI：10.1002/jhet.880

  日期：2012.7

  An efficient and convenient synthesis of substituted 4H‐chromenes is described using room temperature ionic liquid (RTIL) choline chloride–urea in one pot under solvent free conditions. Three‐component Knoevenagel condensation of an aromatic aldehyde, with an active methylene compound, and a cyclohexane dione is reported. This new approach has advantage of excellent yields (82–96%), clean reaction

  在无溶剂条件下，使用室温离子液体（RTIL）氯化胆碱-尿素在一个锅中描述了一种高效便捷的取代4 H-色烯的合成方法。据报道，芳香醛与活性亚甲基化合物和环己烷二酮的三组分Knoevenagel缩合反应。这种新方法的优点是在室温下具有优异的收率（82–96％），干净的反应和较短的反应时间（15–30分钟）。
• 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].