5-amino-4-cyano-3-(o-chlorophenyl)-1H-pyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-4-cyano-3-(o-chlorophenyl)-1H-pyrazole
• 英文别名: 5-amino-3-(2-chloroxyphenyl)-1H-pyrazole-4-carbonitrile；3-amino-5-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile
• 化学式: C₁₀H₇ClN₄
• 分子量: 218.645
• InChiKey: QARYTBIJVCCHSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-4-cyano-3-(o-chlorophenyl)-1H-pyrazole 在 硫酸 作用下， 反应 4.0h， 生成 3-amino-5-(2-chlorophenyl)-1H-pyrazole-4-carboxamide
  参考文献：
  名称：

  Design, Synthesis and Biological Evaluation of 5-Amino-1H-pyrazole-4- carboxamide Derivatives as Potential Antitumor Agents

  摘要：

  已发现腺苷脱氨酶（ADA）抑制剂具有抗肿瘤活性。本文设计、合成了 13 种潜在的腺苷脱氨酶抑制剂 5-氨基-1H-吡唑-4-甲酰胺衍生物，并对其进行了抗肿瘤活性筛选。与其他 5-氨基-1H-吡唑-4-甲酰胺衍生物相比，化合物 8e 对雌激素受体阳性的乳腺癌细胞（MCF-7）具有很强的生长抑制作用和选择性。 此外，它还表现出适当的（μM）腺苷脱氨酶抑制效力。初步的结构-活性关系表明，在吡唑分子的氮原子上加入长链分支是这些衍生物具有活性的原因。

  DOI：

  10.2174/1570180811666140115234123
• 作为产物：
  描述：

  2-[(2-Chloro-phenyl)-methoxy-methylene]-malononitrile 在 一水合肼 作用下， 反应 1.0h， 生成 5-amino-4-cyano-3-(o-chlorophenyl)-1H-pyrazole
  参考文献：
  名称：

  Design, Synthesis and Biological Evaluation of 5-Amino-1H-pyrazole-4- carboxamide Derivatives as Potential Antitumor Agents

  摘要：

  已发现腺苷脱氨酶（ADA）抑制剂具有抗肿瘤活性。本文设计、合成了 13 种潜在的腺苷脱氨酶抑制剂 5-氨基-1H-吡唑-4-甲酰胺衍生物，并对其进行了抗肿瘤活性筛选。与其他 5-氨基-1H-吡唑-4-甲酰胺衍生物相比，化合物 8e 对雌激素受体阳性的乳腺癌细胞（MCF-7）具有很强的生长抑制作用和选择性。 此外，它还表现出适当的（μM）腺苷脱氨酶抑制效力。初步的结构-活性关系表明，在吡唑分子的氮原子上加入长链分支是这些衍生物具有活性的原因。

  DOI：

  10.2174/1570180811666140115234123

文献信息

• Novel biocompatible glucose-based deep eutectic solvent as recyclable medium and promoter for expedient multicomponent green synthesis of diverse three and four substituted pyrazole-4-carbonitrile derivatives
  作者：Reza Aryan、Hamid Beyzaei、Masoomeh Nojavan、Meysam Rezaei

  DOI：10.1007/s11164-017-2908-5

  日期：2017.8

  A novel biocompatible glucose-based deep eutectic solvent (DES) is reported for the first time in the multicomponent synthesis of diverse three and four substituted pyrazole-4-carbonitrile derivatives under catalyst-free condition without using any harmful organic solvent even for purification of the products. The desired products were obtained with high degree of diversity from the reaction of malononitrile

  首次报道了一种新型的生物相容性的基于葡萄糖的深共熔溶剂（DES），该多组分合成是在无催化剂的条件下不使用任何有害有机溶剂甚至无需纯化任何三价或四价取代的吡唑-4-腈衍生物而进行的多组分合成。产品。从丙二腈，芳族醛和各种肼衍生物作为氮源，在室温下，在较短的反应时间内，以良好的产率获得了具有高度多样性的所需产物。还将深的低共熔溶剂再循环并重复使用至少四次，而效率仅有一点损失。还提出了一个合理的机制，表明DES氢键在反应促进中的作用。
• The conversion of isothiazoles into pyrazoles using hydrazine
  作者：Heraklidia A. Ioannidou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2009.06.041

  日期：2009.8

  The conversion of isothiazoles into pyrazoles on treatment with hydrazine is investigated. The influence of various C-3, C-4 and C-5 isothiazole substituents and some limitations of this ring transformation are examined. When the isothiazole C-3 substituent is a good nucleofuge, 3-aminopyrazoles are obtained. However, when the 3-substituent is not a leaving group it is retained in the pyrazole product. Treatment of 4-bromo-3-chloro-5-phenylisothiazoie 56 or 3-chloro-4,5-diphenylisothiazole 57 with anhydrous hydrazine at ca. 200 degrees C for a few minutes gives the corresponding 3-hydrazinoisothiazoles 61 and 64 respectively in high yields; the stability of these new hydrazines is investigated. 5,5'-Diphenyl-3,3'-biisothiazole-4,4'-dicarbonitrile 78 reacts with hydrazine to give 5,5'-diphenyl-3,3'-bi(1H-pyi-azole)-4,4'-dicarbonitrile 79. Methylhydrazine reacts with 3-chloro-5-phenytisothiazole-4-carbonitrile 1 to give 3-(1-methylhydrazino)-5-phenylisothiazole-4-carbontrile 83 and 3-amino-lmethyl-5-phenylpyrazole-4-carbonitrile 84. All products are fully characterised and rational mechanisms for the isothiazole into pyrazole transformation are proposed. (C) 2009 Elsevier Ltd. All rights reserved.
• ——
  作者：Xiao-Hong Zhang、Lin-Hong Weng、Gui-Yu Jin

  DOI：10.1023/a:1013224308504

  日期：——

  The title compound 1-(1',3'-dimethyl-5'-chloropyrazol-4'-carbonyl)-3-(2'-chlorophenyl)-5-amino-4-cyanopyrazole (C16H12Cl2N6O) has been synthesized and characterized by X-ray diffraction: Triclinic, space group P1, with a = 8.6712(8) Angstrom, b = 9.5091(10) Angstrom, c = 11.2170(11) Angstrom; alpha = 71.531(2), beta = 84.683(2), gamma = 74.099(2); Z = 2; V = 843.7(14) Angstrom(3). C(10), O(1), C(11), and N(2) atoms are coplanar with the average deviation of 0.0071Angstrom, which form 11.03degrees and 43.93degrees dihedral angles with pyrazole planes (I) and (II), respectively.
• Design, Synthesis and Biological Evaluation of 5-Amino-1H-pyrazole-4- carboxamide Derivatives as Potential Antitumor Agents
  作者：Baowei Yang、Wukun Liu、Yicheng Mei、Dandan Huang、Hai Qian、Wenlong Huang、Ronald Gust

  DOI：10.2174/1570180811666140115234123

  日期：2014.5.31

  Adenosine deaminase (ADA) inhibitors have been found to have antitumor activities. Here, thirteen potential adenosine deaminase inhibitors 5-amino-1H-pyrazole-4-carboxamide derivatives were designed, synthesized and screened for antitumor activities. Compound 8e exhibited strong growth-inhibitory effects which showed selectivity toward the estrogen receptor positive breast cancer cells (MCF-7) compared to other 5-amino-1H-pyrazole-4-carboxamide derivatives. In addition, it also exhibited appropriate (μM) adenosine deaminase inhibitory potency. Preliminary structure-activity relationships indicated that the incorporation of long chain branching on nitrogen atoms at pyrazole moiety was responsible for their activity.

  已发现腺苷脱氨酶（ADA）抑制剂具有抗肿瘤活性。本文设计、合成了 13 种潜在的腺苷脱氨酶抑制剂 5-氨基-1H-吡唑-4-甲酰胺衍生物，并对其进行了抗肿瘤活性筛选。与其他 5-氨基-1H-吡唑-4-甲酰胺衍生物相比，化合物 8e 对雌激素受体阳性的乳腺癌细胞（MCF-7）具有很强的生长抑制作用和选择性。 此外，它还表现出适当的（μM）腺苷脱氨酶抑制效力。初步的结构-活性关系表明，在吡唑分子的氮原子上加入长链分支是这些衍生物具有活性的原因。