1-phenyl-3-methyl-1H-pyrazole-5-carbonyle chloride

• 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-phenyl-3-methyl-1H-pyrazole-5-carbonyle chloride
• 英文别名: 3-methyl-1-phenyl-1H-pyrazole-5-carbonyl chloride；5-methyl-2-phenyl-2H-pyrazole-3-carbonyl chloride；5-Methyl-2-phenyl-2H-pyrazol-3-carbonylchlorid；5-methyl-2-phenylpyrazole-3-carbonyl chloride
• 化学式: C₁₁H₉ClN₂O
• 分子量: 220.658
• InChiKey: MWQCNQXAKUYTJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-methyl-1H-pyrazole-5-carbonyle chloride 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 34.0h， 生成 N-(2-aminophenyl)-N,3-dimethyl-1-phenyl-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  10.3998/ark.5550190.0015.407

  摘要：

  DOI：

  10.3998/ark.5550190.0015.407
• 作为产物：
  描述：

  乙酰丙酮酸乙酯 在 氯化亚砜 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 10.5h， 生成 1-phenyl-3-methyl-1H-pyrazole-5-carbonyle chloride
  参考文献：
  名称：

  靶向EcR / USP受体的新型取代吡唑酰胺衍生物的设计，合成和生物学活性

  摘要：

  摘要为了发现高活性蜕皮激素类似物，在两种活性化合物N-（3）的核心结构的基础上，采用结构导向的优化方法，获得了一系列新的取代吡唑酰胺衍生物，并对其杀虫活性进行了筛选。 -甲氧基苯基）-3-（叔丁基）-1-苯基-1H-吡唑-5-羧酰胺（6e）和N-（4-（叔丁基）苯基）-3-（叔丁基）-1-苯基-1H-吡唑-5-羧酰胺（6i），以前由我们提供。通过光谱分析鉴定标题化合物的化学结构。初步的生物测定结果表明，合成的吡唑衍生物中的一种，化合物34，对Mythimna Separata的活性为10 mg / L，与阳性对照tebufenozide的活性相当。此外，分子对接和分子动力学研究的例子表明，34可能是EcR的潜在抑制剂，其对接构象与tebufenozide相似。另外，增加疏水作用并考虑对吡唑环的合适的整体作用有利于抑制EcR的活性和体内活性。

  DOI：

  10.1016/j.cclet.2016.02.009

文献信息

• Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring
  作者：Zhongzhong Yan、Aiping Liu、Mingzhi Huang、Minhua Liu、Hui Pei、Lu Huang、Haibo Yi、Weidong Liu、Aixi Hu

  DOI：10.1016/j.ejmech.2018.02.036

  日期：2018.4

  Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole

  吡唑甲酰胺类杀菌剂是最重要的农业杀菌剂之一，属于琥珀酸脱氢酶抑制剂（SDHIS）。为发现具有广谱和高活性的新型吡唑羧酰胺类似物，通过支架跳跃和生物立体异构化设计了一类新型的含噻唑或恶唑环的吡唑羧酰胺衍生物，合成了36种具有抗真菌活性的吡唑羧酰胺衍生物。对这些化合物针对五种植物病原真菌，玉米赤霉菌，辣椒疫霉菌，菌核盘菌，小粒小麦和高粱锈菌进行了评估。结果表明，大多数化合物表现出良好的杀真菌活性，特别是对E. graminis。理论计算是在B3LYP / 6-31G上进行的（d，
• Discovery of N -[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2- b ]pyridazin-6-yl}oxy)-2-methylphenyl]-1,3-dimethyl-1 H -pyrazole-5-carboxamide (TAK-593), a highly potent VEGFR2 kinase inhibitor
  作者：Naoki Miyamoto、Nozomu Sakai、Takaharu Hirayama、Kazuhiro Miwa、Yuya Oguro、Hideyuki Oki、Kengo Okada、Terufumi Takagi、Hidehisa Iwata、Yoshiko Awazu、Seiji Yamasaki、Toshiyuki Takeuchi、Hiroshi Miki、Akira Hori、Shinichi Imamura

  DOI：10.1016/j.bmc.2013.01.074

  日期：2013.4

  for the treatment of cancer. In this study, we describe the design, synthesis, and biological evaluation of 2-acylamino-6-phenoxy-imidazo[1,2-b]pyridazine derivatives. Hybridization of two distinct imidazo[1,2-b]pyridazines 1 and 2, followed by optimization led to the discovery of N-[5-(2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-methylphenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide

  血管内皮生长因子（VEGF）在肿瘤血管生成中起着重要作用，抑制其信号传导途径被认为是治疗癌症的有效治疗选择。在这项研究中，我们描述了2-酰基氨基-6-苯氧基-咪唑并[1,2- b ]哒嗪衍生物的设计，合成和生物学评估。两种不同的咪唑并[1,2- b ]哒嗪1和2杂交，然后进行优化导致发现N- [5-（2-[（环丙基羰基）氨基]咪唑并[1,2- b ]哒嗪- 6-基}氧基）-2-甲基苯基] -1,3-二甲基-1 H-吡唑-5-羧酰胺（23a（TAK-593）作为一种高效的VEGF受体2激酶抑制剂，IC 50值为0.95 nM。化合物23a以0.30 nM的IC 50强烈抑制了VEGF刺激的人脐静脉内皮细胞的增殖。激酶选择性分析显示23a抑制了血小板衍生的生长因子受体激酶以及VEGF受体激酶。在使用人肺腺癌A549细胞的小鼠异种移植模型中，口服1mg / kg的23a可以有效抑制肿瘤的生长（T
• Synthesis and biofilm formation reduction of pyrazole-4-carboxamide derivatives in some Staphylococcus aureus strains
  作者：Stella Cascioferro、Benedetta Maggio、Demetrio Raffa、Maria Valeria Raimondi、Maria Grazia Cusimano、Domenico Schillaci、Barbara Manachini、Fabiana Plescia、Giuseppe Daidone

  DOI：10.1016/j.ejmech.2016.07.030

  日期：2016.11

  The ability of several N-phenyl-1H-pyrazole-4-carboxamide derivatives and other pyrazoles opportunely modified at the positions 3, 4 and 5, to reduce the formation of the biofilm in some Staphylococcus aureus strains (ATCC 29213, ATCC 25923 and ATCC 6538) were investigated. All the tested compounds were able, although to a different extent, to reduce the biofilm formation of the three bacterial strains

  在3、4和5位适当修饰的一些N-苯基-1H-吡唑-4-羧酰胺衍生物和其他吡唑的能力，以减少某些金黄色葡萄球菌菌株（ATCC 29213，ATCC 25923和ATCC）中生物膜的形成6538）进行了调查。尽管程度不同，所有测试的化合物均能够减少所考虑的三种细菌菌株的生物膜形成。其中，1-（2,5-二氯苯基）-5-甲基-N-苯基-1H-吡唑-4-羧酰胺14是生物膜形成的最佳抑制剂，对所有化合物的IC50范围为2.3至32μM。金黄色葡萄球菌的三种菌株。化合物14还通过提高感染金黄色葡萄球菌ATCC 29213的蜡蛾幼虫（Galleria mellonella）的存活率而在体内显示出良好的保护作用。
• New Analogues of (<i>E</i>)-β-Farnesene with Insecticidal Activity and Binding Affinity to Aphid Odorant-Binding Proteins
  作者：Yufeng Sun、Huili Qiao、Yun Ling、Shaoxiang Yang、Changhui Rui、Paolo Pelosi、Xinling Yang

  DOI：10.1021/jf104712c

  日期：2011.3.23

  (E)-beta-Farnesene is a strong and efficient alarm pheromone in most aphid species. However, applications in agriculture are prevented by its relatively high volatility, its susceptibility to oxidation and its complex and expensive synthesis. To develop novel compounds for aphid control, we have designed and synthesized analogues of (E)-beta-famesene, containing a pyrazole moiety present in several insecticides. Their structures have been confirmed by (1)H NMR, elemental analysis, high-resolution mass spectroscopy and IR. Binding activities to three odorant-binding proteins (OBPs) of the pea aphid Acythosiphon pisum have been evaluated and correlated with their structures with reference to (E)-beta-famesene. Several derivatives were shown both to bind to A. pisum OBPs with a specificity similar to that of (E)-beta-famesene and to have aphicidal activity comparable to that of thiacloprid, a commercial insecticide. The compounds synthesized in this work represent new potential agents for aphid population control and provide guidelines to design analogues of (E)-beta-famesene endowed with both insecticidal and repellent activity for aphids.

  (E)-β-НАРСЕС is a strong and efficient ALARM PHENOMONE in most aphid species. However, its applications in agriculture are hindered by its relatively high VOLATILITY, susceptibility to OXIDATION, and complex and costly SYNTHESIS. In an effort to develop novel chemical entities for aphid CONTROL, we have designed and synthesized ANALOGUES of (E)-β-НАРСЕС, each bearing a PYRAZOLE moiety, a structural feature commonly found in several INSECTICIDES. Their structural analyses have been confirmed via (1)H NMR, ELEMENTAL ANALYSIS, HIGH-RESOLUTION MASS SPECTROSCOPY, and INFRARED SPECTROSCOPY. Binding activities to three ODDOR glVertex proteins (OBVs) of the pea aphid Acythosiphon pisum have been evaluated and correlative with the compounds' structures as a reference to (E)-β-НАРСЕС. Several derivatives were found to bind to A. pisum OBDs with a specificity comparable to that of (E)-β-НАРСЕС and exhibited ENTICING activity akin to that of thiacloprid, a widely used COMMERCIAL INSECTICIDE. The compounds synthesized in this study represent novel POTENTIAL AGENTS for POPULATION CONTROL of aphids and offer guidance for the design of ANALOGS of (E)-β-НАРСЕES endowed with both INSECTICIDAL and repellent properties for aphids.
• Design, synthesis and biological evaluation of 1H-pyrazole-5-carboxamide derivatives as potential fungicidal and insecticidal agents
  作者：Danling Huang、Mingzhi Huang、Weidong Liu、Aiping Liu、Xingping Liu、Xiaoyang Chen、Hui Pei、Jiong Sun、Dulin Yin、Xiaoguang Wang

  DOI：10.1007/s11696-017-0198-4

  日期：2017.11

  Bioassay results showed that most of the title compounds showed potent fungicidal activities against Erysiphe graminis and insecticidal activity against Aphis fabae. Especially, compound 9b has EC50 values of 3.04 mg/L against Erysiphe graminis, of which the fungicidal activity is better than that of the commercial fungicide Thifluzamide and Azoxystrobinare; compound 9l has LC50 values of 3.81 mg/L

  摘要通过简便的方法设计和合成了一系列含有苯基噻唑部分的新型1H-吡唑-5-羧酰胺化合物，并通过1 H NMR，质谱和元素分析对其结构进行了表征。生物测定结果表明，大多数标题化合物显示强大的杀菌活性对小麦白粉病和抗杀虫活性蚜蚜。特别是，化合物9B具有EC 50为3.04毫克值/ L抵抗禾白粉菌，其中的杀真菌活性比商业杀真菌剂和的Thifluzamide的Azoxystrobinare更好; 化合物9l的LC 50蚜虫的3.81 mg / L的值与商业杀虫剂Tolfenpyrad相当。建议将含有苯基噻唑部分的1H-吡唑-5-羧酰胺化合物视为进一步设计农药的前体结构。 图形概要通过简便的方法设计和合成了一系列含有苯基噻唑部分的新型1H-吡唑-5-羧酰胺化合物，并通过1 H NMR，质谱和元素分析对其结构进行了表征。生物测定结果表明，大多数标题化合物显示强大的杀菌活性对小麦白粉病和抗杀虫活性蚜蚜。特别是，化合物9B具有EC