1-(4-methoxyphenyl)-3-methylchromeno[4,3-c]pyrazol-4(1H)-one | 110570-27-9

• 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-(4-methoxyphenyl)-3-methylchromeno[4,3-c]pyrazol-4(1H)-one
• 英文别名: 1-(4-Methoxyphenyl)-3-methylchromeno[4,3-c]pyrazol-4-one
• CAS: 110570-27-9
• 化学式: C₁₈H₁₄N₂O₃
• 分子量: 306.321
• InChiKey: PKYREBDGJZHJCV-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172 °C
• 沸点：
  510.2±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基苯肼盐酸盐 在 对甲苯磺酸 作用下， 以 乙醇 、 xylene 为溶剂， 生成 1-(4-methoxyphenyl)-3-methylchromeno[4,3-c]pyrazol-4(1H)-one
  参考文献：
  名称：

  中心苯并二氮杂receptor受体配体1-芳基和2-芳基[1]苯并吡喃并唑-4-酮的合成，结合研究及构效关系。

  摘要：

  DOI：

  10.1021/jm00396a001

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
• Copper-catalyzed Cyclization of 3-Acylcoumarin Hydrazone using Air as the Oxidant: Efficient Synthesis of Pyrazole-Fused Coumarin Derivatives
  作者：Hui-Yan Wang、Xue-Cheng Liu、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1002/jhet.2052

  日期：2015.3

  3‐c]pyrazol‐4(1H)‐ones is reported. In this atom economic process, readily available 3‐acylcoumarin hydrazone is oxidative cyclized by direct C–N bond formation. Air has been successfully used as an oxidant, which has important economic and environmental advantages. A broad scope of 3‐acylcoumarin hydrazones can be utilized in this process.

  据报道，高效，便捷的Cu催化形成了铬诺[4,3 - c ]吡唑-4（1 H）-酮。在这个原子经济过程中，容易获得的3酰基香豆素通过直接的C–N键形成而被氧化环化。空气已成功地用作氧化剂，具有重要的经济和环境优势。在此过程中，可以使用各种3-酰基香豆素。
• Synthesis, anticancer activity and photophysical properties of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates
  作者：J. Ashok Kumar、G. Saidachary、G. Mallesham、B. Sridhar、Nishant Jain、Shashi Vardhan Kalivendi、V. Jayathirtha Rao、B. China Raju

  DOI：10.1016/j.ejmech.2013.03.042

  日期：2013.7

  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.
• Microwave-Assisted Synthesis of 3-Methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones under Solvent-Free Conditions
  作者：Cui-Lian Xu、Guo-Yu Yang、Jing-Tian Yang、Cai-Xia Wang、Su-Fang Fan、Pu-Hui Xie

  DOI：10.3987/com-13-12719

  日期：——
• Facile synthesis of pyrazole derivatives using reusable Fe3O4@MCM-41-SO3H
  作者：Samanehsadat Sharifi、Malek Taher Maghsoudlou、Nourallah Hazeri

  DOI：10.1139/cjc-2019-0287

  日期：2021.5

  In this research, Fe3O4-MCM-41-SO3H was synthesized as a magnetically reusable Lewis acid catalyst and used in the cyclization reaction of 3-acylcoumarins or 3-chromonecarboxylic acid with arylhydrazine derivatives for the synthesis of pyrazoles in high yields under solvent-free conditions and with a simple work-up process. Fe3O4-MCM-41-SO3H was characterized by Fourier transform infrared (FTIR), scanning electron microscopy (SEM), and X‐ray diffraction (XRD) analyses.