4-chloro-3-ethyl-N-(4-hydroxybenzyl)-1-methyl-1H-pyrazole-5-carboxamide | 1374595-90-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-chloro-3-ethyl-N-(4-hydroxybenzyl)-1-methyl-1H-pyrazole-5-carboxamide
• 英文别名: 4-chloro-5-ethyl-N-[(4-hydroxyphenyl)methyl]-2-methylpyrazole-3-carboxamide
• CAS: 1374595-90-0
• 化学式: C₁₄H₁₆ClN₃O₂
• 分子量: 293.753
• InChiKey: OKMQAJCJGNYAID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-3-ethyl-N-(4-hydroxybenzyl)-1-methyl-1H-pyrazole-5-carboxamide 在 copper(l) iodide 、 对甲酚 、 N,N-二甲基甘氨酸 、 四溴化碳 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-(4-(4-(azidomethyl)phenoxy)benzyl)-4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  Structure–Activity Relationship Studies of Tolfenpyrad Reveal Subnanomolar Inhibitors ofHaemonchus contortusDevelopment

  摘要：

  Recently, we have discovered that the registered pesticide, tolfenpyrad, unexpectedly and potently inhibits the development of the L4 larval stage of the parasitic nematode Haemonchus contortus with an IC50 value of 0.03 mu M while displaying good selectivity, with an IC50 of 37.9 mu M for cytotoxicity. As a promising molecular template for medicinal chemistry optimization, we undertook anthelmintic structure-activity relationships for this chemical. Modifications of the left-hand side (LHS), right-hand side (RHS), and middle section of the scaffold were explored to produce a set of 57 analogues. Analogues 25, 29, and 33 were shown to be the most potent compounds of the series, with IC50 values at a subnanomolar level of potency against the chemotherapeutically relevant fourth larval (L4) stage of H. contortus. Selected compounds from the series also showed promising activity against a panel of other different parasitic nematodes, such as hookworms and whipworms.

  DOI：

  10.1021/acs.jmedchem.8b01789
• 作为产物：
  描述：

  4-氯-3-乙基-1-甲基-1H-吡唑-5-甲酰氯 、 4-羟基苄胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85.2%的产率得到4-chloro-3-ethyl-N-(4-hydroxybenzyl)-1-methyl-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  PYRAZOLE AMIDE COMPOUNDS AND USES THEREOF

  摘要：

  本发明揭示了一种具有杀真菌活性的吡唑酰胺化合物，其结构由通式（I）所示：化合物的每个取代基均如描述中所定义。本发明的化合物具有杀真菌活性，并对瓜类霜霉病、玉米锈病、小麦白粉病、水稻稻瘟等疾病具有优异的预防和控制效果，尤其对瓜类霜霉病和玉米锈病有更好的预防和控制效果。还公开了一种制备该化合物的方法，含有通式（I）化合物的杀真菌组合物以及其在农作物疾病预防和控制中的应用。

  公开号：

  US20130225585A1

文献信息

• PYRAZOLE AMIDE COMPOUND AND USE THEREOF
  申请人：Sinochem Corporation

  公开号：EP2636669A1

  公开（公告）日：2013-09-11

  Disclosed is a pyrazole amide compound having fungicidal activity, with a structure shown by the general formula (I): Each of the substituents of the compound being defined as in the description. The compound of the present invention has fungicidal activity, and excellent prevention and controlling effects on diseases, such as cucumber downy mildew, corn rust, wheat powdery mildew, rice blast, etc., and in particular, a better prevention and controlling effect on cucumber downy mildew and corn rust. Also disclosed is a process for preparing the compound, a fungicidal composition containing the compound of general formula(I) and the use thereof in preventing and controlling disease in crops.

  本发明公开了一种具有杀菌活性的吡唑酰胺化合物，其结构如通式（I）所示： 化合物中各取代基的定义见说明。本发明的化合物具有杀菌活性，对黄瓜霜霉病、玉米锈病、小麦白粉病、稻瘟病等病害有很好的防治效果，特别是对黄瓜霜霉病和玉米锈病有较好的防治效果。还公开了一种制备该化合物的工艺、一种含有通式（I）化合物的杀菌组合物及其在防治作物病害中的用途。
• PYRAZOLE AMIDE COMPOUND AND USE THEREOF AS FUNGICIDE
  申请人：Sinochem Corporation

  公开号：EP2636669B1

  公开（公告）日：2015-10-21
• Structure–Activity Relationship Studies of Tolfenpyrad Reveal Subnanomolar Inhibitors of<i>Haemonchus contortus</i>Development
  作者：Thuy G. Le、Abhijit Kundu、Atanu Ghoshal、Nghi H. Nguyen、Sarah Preston、Yaqing Jiao、Banfeng Ruan、Lian Xue、Fei Huang、Jennifer Keiser、Andreas Hofmann、Bill C. H. Chang、Jose Garcia-Bustos、Timothy N. C. Wells、Michael J. Palmer、Abdul Jabbar、Robin B. Gasser、Jonathan B. Baell

  DOI：10.1021/acs.jmedchem.8b01789

  日期：2019.1.24

  Recently, we have discovered that the registered pesticide, tolfenpyrad, unexpectedly and potently inhibits the development of the L4 larval stage of the parasitic nematode Haemonchus contortus with an IC50 value of 0.03 mu M while displaying good selectivity, with an IC50 of 37.9 mu M for cytotoxicity. As a promising molecular template for medicinal chemistry optimization, we undertook anthelmintic structure-activity relationships for this chemical. Modifications of the left-hand side (LHS), right-hand side (RHS), and middle section of the scaffold were explored to produce a set of 57 analogues. Analogues 25, 29, and 33 were shown to be the most potent compounds of the series, with IC50 values at a subnanomolar level of potency against the chemotherapeutically relevant fourth larval (L4) stage of H. contortus. Selected compounds from the series also showed promising activity against a panel of other different parasitic nematodes, such as hookworms and whipworms.
• PYRAZOLE AMIDE COMPOUNDS AND USES THEREOF
  申请人：Liu Changling

  公开号：US20130225585A1

  公开（公告）日：2013-08-29

  Disclosed is a pyrazole amide compound having fungicidal activity, with a structure shown by the general formula (I): Each of the substituents of the compound being defined as in the description. The compound of the present invention has fungicidal activity, and excellent prevention and controlling effects on diseases, such as cucumber downy mildew, corn rust, wheat powdery mildew, rice blast, etc., and in particular, a better prevention and controlling effect on cucumber downy mildew and corn rust. Also disclosed is a process for preparing the compound, a fungicidal composition containing the compound of general formula (I) and the use thereof in preventing and controlling disease in crops.

  本发明揭示了一种具有杀真菌活性的吡唑酰胺化合物，其结构由通式（I）所示：化合物的每个取代基均如描述中所定义。本发明的化合物具有杀真菌活性，并对瓜类霜霉病、玉米锈病、小麦白粉病、水稻稻瘟等疾病具有优异的预防和控制效果，尤其对瓜类霜霉病和玉米锈病有更好的预防和控制效果。还公开了一种制备该化合物的方法，含有通式（I）化合物的杀真菌组合物以及其在农作物疾病预防和控制中的应用。