6-Amino-4-(2,3-dichlorophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile | 309926-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-Amino-4-(2,3-dichlorophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 6-amino-4-(2,3-dichlorophenyl)-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• CAS: 309926-39-4；311333-39-8
• 化学式: C₁₄H₁₀Cl₂N₄O
• 分子量: 321.166
• InChiKey: BLHYEELNFZODMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  563.0±50.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Amino-4-(2,3-dichlorophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile 、 环己酮 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以82%的产率得到4-(2,3-dichlorophenyl)-3-methyl-2,4,6,7,8,9-hexahydropyrazolo[4',3':5,6]pyrano[2,3-b]quinolin-5-amine
  参考文献：
  名称：

  New tetracyclic tacrine analogs containing pyrano[2,3-c]pyrazole: Efficient synthesis, biological assessment and docking simulation study

  摘要：

  A new series of tacrine-based acetylcholinesterase (AChE) inhibitors 7a-1 were designed by replacing the benzene ring of tacrine with aryl-dihydropyrano[2,3-c]pyrazole. The poly-functionalized hybrid molecules 7a-1 were efficiently synthesized through multi-component reaction and subsequent Friedlander reaction between the obtained pyrano[2,3-c]pyrazoles and cyclohexanone. Most of target compounds showed potent and selective anti-AChE activity at sub-micromolar range. The most potent compound 7h bearing a 3,4-dimethoxyphenyl group was more active than reference drug tacrine. The representative compound 7h could significantly protect neurons against oxidative stress as potent as quercetin at low concentrations. The docking study of compound 7h with AChE enzyme revealed that the (R)-enantiomer binds preferably to CAS while the (S)-enantiomer prone to be a PAS binder. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.049
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2,3-二氯苯甲醛 、 丙二腈 在 hydrazine hydrate 作用下， 以 水 为溶剂， 反应 0.5h， 以95%的产率得到6-Amino-4-(2,3-dichlorophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  磁性 MCM-41 上稳定的 3,4-二氨基二苯甲酮铜席夫碱络合物作为四唑和吡喃吡唑合成中的均选择性和可重复使用催化剂

  摘要：

  这项工作讨论了在磁性 MCM-41 上稳定的 3,4-二氨基二苯甲酮的新型席夫碱铜络合物的合成和表征，作为磁性可重复使用的催化剂。首先，在氨的碱性溶液中，通过化学共沉淀法合成了Fe 3 O 4磁性纳米粒子。然后通过Fe 3 O 4合成磁性MCM-41-掺杂到MCM-41的介孔通道中。此外，一种新的 3,4-二氨基二苯甲酮铜席夫碱配合物负载在磁性 MCM-41 上，并在有机反应中用作实用且可磁性重复使用的催化剂，例如四唑和吡喃吡唑衍生物的均选合成。该催化剂通过扫描电子显微镜（SEM）、能量色散X射线光谱（EDS）、波长色散X射线光谱（WDX）、热重分析（TGA）、X射线粉末衍射（XRD）等技术进行表征。 )、原子吸收光谱 (AAS)、傅里叶变换红外光谱 (FT-IR)、Brunauer-Emmett-Teller (BET) 和振动样品磁力计 (VSM)。该催化剂选择性好、活性高、稳定性好、易于磁分离。所以，

  DOI：

  10.1002/aoc.6895

文献信息

• Glycine-Catalyzed Efficient Synthesis of Pyranopyrazoles via One-Pot Multicomponent Reaction
  作者：M. B. Madhusudana Reddy、V. P. Jayashankara、M. A. Pasha

  DOI：10.1080/00397910903340686

  日期：2010.8.31

  A facile and convenient protocol is developed for the fast (5-20min) and high-yielding (85-95%) synthesis of fused pyranopyrazoles from ethyl acetoacetate, hydrazine hydrate, an aldehyde, and malononitrile in the presence of nontoxic, simple, and readily available organocatalyst glycine in aqueous medium at 25 degrees C.
• Rapid four-component reactions in water: synthesis of pyranopyrazoles
  作者：Gnanasambandam Vasuki、Kandhasamy Kumaravel

  DOI：10.1016/j.tetlet.2008.07.055

  日期：2008.9

  An environmentally benign four-component reaction in aqueous medium at room temperature has been developed for the synthesis of 6-amino-5-cyano-3-methyl-4-aryl/heteroaryl-3H,4H-dihydropyrano[2,3,-c]pyrazoles (C) 2008 Elsevier Ltd. All rights reserved.
• New tetracyclic tacrine analogs containing pyrano[2,3-c]pyrazole: Efficient synthesis, biological assessment and docking simulation study
  作者：Mehdi Khoobi、Farzaneh Ghanoni、Hamid Nadri、Alireza Moradi、Morteza Pirali Hamedani、Farshad Homayouni Moghadam、Saeed Emami、Mohsen Vosooghi、Reza Zadmard、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1016/j.ejmech.2014.10.049

  日期：2015.1

  A new series of tacrine-based acetylcholinesterase (AChE) inhibitors 7a-1 were designed by replacing the benzene ring of tacrine with aryl-dihydropyrano[2,3-c]pyrazole. The poly-functionalized hybrid molecules 7a-1 were efficiently synthesized through multi-component reaction and subsequent Friedlander reaction between the obtained pyrano[2,3-c]pyrazoles and cyclohexanone. Most of target compounds showed potent and selective anti-AChE activity at sub-micromolar range. The most potent compound 7h bearing a 3,4-dimethoxyphenyl group was more active than reference drug tacrine. The representative compound 7h could significantly protect neurons against oxidative stress as potent as quercetin at low concentrations. The docking study of compound 7h with AChE enzyme revealed that the (R)-enantiomer binds preferably to CAS while the (S)-enantiomer prone to be a PAS binder. (C) 2014 Elsevier Masson SAS. All rights reserved.
• A new copper Schiff‐base complex of 3,4‐diaminobenzophenone stabilized on magnetic MCM‐41 as a homoselective and reusable catalyst in the synthesis of tetrazoles and pyranopyrazoles
  作者：Tavan Kikhavani、Parisa Moradi、Mohammad Mashari‐Karir、Jalil Naji

  DOI：10.1002/aoc.6895

  日期：2022.12

  mesoporous channels of MCM-41. Further a new copper Schiff-base complex of 3,4-diaminobenzophenone was supported on magnetic MCM-41 and was used as a practical and magnetically reusable catalyst in organic reactions such as homoselective synthesis of tetrazole and pyranopyrazole derivatives. This catalyst was characterized by several techniques such as scanning electron microscopy (SEM), energy-dispersive

  这项工作讨论了在磁性 MCM-41 上稳定的 3,4-二氨基二苯甲酮的新型席夫碱铜络合物的合成和表征，作为磁性可重复使用的催化剂。首先，在氨的碱性溶液中，通过化学共沉淀法合成了Fe 3 O 4磁性纳米粒子。然后通过Fe 3 O 4合成磁性MCM-41-掺杂到MCM-41的介孔通道中。此外，一种新的 3,4-二氨基二苯甲酮铜席夫碱配合物负载在磁性 MCM-41 上，并在有机反应中用作实用且可磁性重复使用的催化剂，例如四唑和吡喃吡唑衍生物的均选合成。该催化剂通过扫描电子显微镜（SEM）、能量色散X射线光谱（EDS）、波长色散X射线光谱（WDX）、热重分析（TGA）、X射线粉末衍射（XRD）等技术进行表征。 )、原子吸收光谱 (AAS)、傅里叶变换红外光谱 (FT-IR)、Brunauer-Emmett-Teller (BET) 和振动样品磁力计 (VSM)。该催化剂选择性好、活性高、稳定性好、易于磁分离。所以，