1-phenylchromeno[4,3-c]pyrazol-4(1H)-one | 51070-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenylchromeno[4,3-c]pyrazol-4(1H)-one
• 英文别名: 1-Phenylchromeno[4,3-c]pyrazol-4-one
• CAS: 51070-05-4
• 化学式: C₁₆H₁₀N₂O₂
• 分子量: 262.268
• InChiKey: FCEYJZUAYRXKOS-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C(Solv: ethanol (64-17-5))
• 沸点：
  464.2±14.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酸苯酯 在 哌啶 、 吡啶 、 aluminum (III) chloride 、 sodium hydride 、 溶剂黄146 、 三氯氧磷 作用下， 以 甲醇 、 水 为溶剂， 反应 4.75h， 生成 1-phenylchromeno[4,3-c]pyrazol-4(1H)-one
  参考文献：
  名称：

  Synthesis, anticancer activity and photophysical properties of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates

  摘要：

  2-Oxo-2H-chromenylpyrazolecarboxylates (8a-h and 12a-zb) have been synthesized by [3 + 2] cycloaddition of 2H-chromenophenylhydrazones (7a-h and 11a-w) with diethyl/dimethylbut-2-ynedioates. Phenylchromeno[4,3-c]pyrazol-4(1H)-ones (13i-n) were prepared from corresponding phenylhydrazones (7a-h) with catalytic amount of piperidine in presence of pyridine as a solvent at 100 degrees C. All the synthesized compounds (8a-h, 12a-zb and 13a-n) were screened for anticancer activity against three human cancer cell lines such as prostate (DU-145), lung adenocarcinoma (A549), and cervical (HeLa) by standard MTT assay method. Further, photophysical properties (UV and fluorescence) for these compounds were discussed. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.042

文献信息

• Structural investigations on coumarins leading to chromeno[4,3-c]pyrazol-4-ones and pyrano[4,3-c]pyrazol-4-ones: New scaffolds for the design of the tumor-associated carbonic anhydrase isoforms IX and XII
  作者：Alessandro Bonardi、Matteo Falsini、Daniela Catarzi、Flavia Varano、Lorenzo Di Cesare Mannelli、Barbara Tenci、Carla Ghelardini、Andrea Angeli、Claudiu T. Supuran、Vittoria Colotta

  DOI：10.1016/j.ejmech.2018.01.033

  日期：2018.2

  tumor-associated hCAs IX and XII and the cytosolic isoforms hCAs I and II. Several compounds were potent (Ki < 41 nM) and selective inhibitors of the hCA IX (13, 14, 19, 21, 25, 31, 33, 37 and 39), some derivatives (6, 11 and 17) were active against both hCA IX and XII isoforms (Ki = 5.6–9.6 nM), while none were effective against the off-target cytosolic hCAs I and II. Some selected inhibitors (6, 11

  人碳酸酐酶（hCAs，EC 4.2.1.1）IX和XII在多种癌症中均过表达，并被视为可用于抗肿瘤治疗的药物靶标，因为它们的抑制作用已显示出可减少肿瘤的生长和转移。一组香豆素衍生物（1-10）和几个被1-芳基和2-芳基取代的chromeno [4,3-c]吡唑-4-酮（11-37）和吡喃并[4,3-c] pyrazol-合成了4-ones（38–39），并针对与肿瘤相关的hCAs IX和XII以及胞质亚型hCAs I和II进行了测试。一些化合物有效的（K我 <41纳米）和（所述Hca IX的选择性抑制剂13，14，19，21，25，31，33，37和39），一些衍生物（6，11和17）反对两者HCA IX和XII的同种型（K活性我 = 5.6-9.6纳米），而没有一个是针对脱靶胞质HCAS我有效和二。一些选定的抑制剂（6，11，13，19，21，25，31和39）在常氧和低氧条件下均对HT
• Ring Transformation of Chromone-3-Carboxamide under Nucleophilic Conditions
  作者：Magdy A. Ibrahim

  DOI：10.5935/0103-5053.20130220

  日期：——

  The chemical reactivity of chromone-3-carboxamide was studied towards a series of nitrogen and carbon nucleophiles. Treatment of carboxamide with some primary amines gave chromane-2,4-diones. Condensation of carboxamide with hydrazine hydrate, phenyl hydrazine and hydroxylamine hydrochloride afforded chromenopyrazoles and chromenoisoxazole, respectively. Reaction of carboxamide with guanidine hydrochloride

  研究了色酮-3-羧酰胺对一系列氮和碳亲核试剂的化学反应性。用一些伯胺处理羧酰胺，得到苯并吡喃-2,4-二酮。羧酰胺与水合肼，苯基肼和羟胺盐酸盐的缩合分别提供了色诺吡唑和色诺异恶唑。羧酰胺与盐酸胍，氰基胍和硫脲的反应导致环转化，生成色吡啶。还研究了羧酰胺对乙二胺，邻苯二胺，2-氨基苯酚和2-氨基硫酚的化学行为。从羧酰胺与一些碳亲核试剂的反应中分离出多种产物。
• Synthesis of New Substituted Chromen[4,3-c]pyrazol-4-ones and Their Antioxidant Activities
  作者：Abdullah Sulaiman Al-Ayed

  DOI：10.3390/molecules161210292

  日期：——

  A series of new coumarin derivatives 4 containing a 4-arylbut-3-en-2-one moiety were synthesized by condensation of 3-acetylcoumarin 1 with aryl aldehydes 2 in chloroform in the presence of piperidine. The interactions of 3-formyl-4-chlorocoumarin (3) with nitrogen-containg nucleophiles leading to the corresponding substituted chromen-[4,3-c]pyrazol-4-ones 5 are described. The structures of the obtained compounds were established on the basis of 1D NMR, 2D NMR and IR and further the compounds were evaluated for possible antioxidant activities. The coumarinic chalcone 4a has been found to be the most active (IC50 = 2.07 μM) in this study.

  在哌啶存在下，3-乙酰基香豆素 1 与芳基醛 2 在氯仿中缩合，合成了一系列含有 4-芳基丁-3-烯-2-酮分子的新型香豆素衍生物 4。文中描述了 3-甲酰基-4-氯香豆素（3）与含氮亲核物的相互作用，从而得到相应的取代色烯-[4,3-c]吡唑-4-酮 5。根据一维核磁共振、二维核磁共振和红外光谱确定了所获化合物的结构，并进一步评估了这些化合物可能具有的抗氧化活性。研究发现，香豆素查尔酮 4a 的活性最高（IC50 = 2.07 μM）。
• 4-Oxo-1H-and-2H-[1]benzopyrano[4,3-c]pyrazoles. Preparation from 4-hydroxycoumarin or 3-chromonecarboxylic acid derivatives.
  作者：Bernard Chantegrel、Abdel-Ilah Nodi、Suzanne Gelin

  DOI：10.1016/s0040-4039(00)81413-6

  日期：——

  The conversion of 3-acyl-4-hydroxycoumarins to either 4-oxo-1-phenyl-1H-[1]benzopyrano[4,3-c]pyrazoles or 4-oxo-2-phenyl-2H-[1]benzopyrano[4,3-c]pyrazoles is described. The product obtained from the reaction of phenylhydrazine with 3-chromonecarboxylic acid has been established not to be such 2-phenyl[1]benzopyrano[4,3-c]pyrazol-3-2H-one as previously reported but to be 4-oxo-1-phenyl-1H[1]benzopyrano[4

  3-酰基-4-羟基香豆素转化为4-氧代-1-苯基-1H- [1]苯并吡喃并[4,3-c]吡唑或4-氧代-2-苯基-2H- [1]苯并吡喃[描述了4，3-c]吡唑。已经确定由苯肼与3-色酮羧酸反应获得的产物不是先前报道的2-苯基[1]苯并吡喃并[4,3-c]吡唑-3-2H-酮，而是4-氧代。 -1-苯基-1H [1]苯并吡喃并[4,3-c]吡唑。我们的结果表明，以前描述为从4-氯-3-甲酰基-香豆素中收率的方法是不可行的。
• On the reaction of 3-cyanochromones with phenyl- and methylhydrazines: Structural revision and a simple synthesis of chromeno[4,3-c]pyrazol-4-ones
  作者：Vyacheslav Ya. Sosnovskikh、Vladimir S. Moshkin、Mikhail I. Kodess

  DOI：10.1002/jhet.370

  日期：——

  Reactions of 3‐cyanochromones with phenylhydrazine gave the corresponding 5‐amino‐4‐salicyloyl‐1‐phenylpyrazoles, 2‐aminochromone‐3‐carbaldehyde N‐phenylhydrazones, and 1‐phenylchromeno[4,3‐c]pyrazol‐4(1H)‐one, depending on the reaction conditions. With methylhydrazine, 3‐(2‐hydroxyaryl)‐1‐methylpyrazole‐4‐carbonitriles and 2‐methylchromeno[4,3‐c]pyrazol‐4(2H)‐ones were obtained in moderate to high

  3-氰基色酮与苯肼的反应产生了相应的5-氨基-4-水杨酰基-1-苯基吡唑，2-氨基色酮-3-甲醛N-苯基hydr和1-苯基色[4,3 - c ]吡唑-4（1 H一），具体取决于反应条件。用甲基肼可以中等至高收率获得3-（2-羟基芳基）-1-甲基吡唑-4-腈和2-甲基色[4,3 - c ]吡唑-4-（2 H）一。J.杂环化​​学。（2010）。