N-(4-methylphenyl)-2-oxocyclohexylsulfonamide | 925234-51-1

• 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: N-(4-methylphenyl)-2-oxocyclohexylsulfonamide
• 英文别名: N-(4-methylphenyl)-2-oxocyclohexane-1-sulfonamide
• CAS: 925234-51-1
• 化学式: C₁₃H₁₇NO₃S
• 分子量: 267.349
• InChiKey: SRSGCGKHTHZMPE-UHFFFAOYSA-N

物化性质

• 沸点：
  436.9±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methylphenyl)-2-oxocyclohexylsulfonamide 在 sodium tetrahydroborate 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 以80%的产率得到2-hydroxy-N-(4-methylphenyl)cyclohexane-1-sulfonamide
  参考文献：
  名称：

  Synthesis, Fungicidal Activity, and Structure−Activity Relationship of 2-Oxo- and 2-Hydroxycycloalkylsulfonamides

  摘要：

  To explore new potential fungicides, a series of novel compounds, including 11 2-oxocycloalkylsulfonamide (3) and 21 2-hydroxycycloalkylsulfonamide (4) derivatives, were synthesized and their structures were confirmed by H-1 nuclear magnetic resonance (NMR), infrared (IR), and elemental analysis. The results of the bioassay showed that the compounds 3 and 4 possessed excellent fungicidal activity against Botrytis cinerea Pers. both in vitro and in vivo. The fungicidal activity of the compounds with 7- or 8-membered rings is better than those with 5-, 6-, or 12-membered rings. According to the results of the mycelium growth rate test, the EC50 values of the compounds 3C, 4C, 3D, and 40 were 0.80, 0.85, 1.22, and 1.09 mu g/mL, respectively, and similar to or better than commercial fungicide procymidone. The bioassay results of spore germination indicated that most of the compounds exhibited obvious inhibitory effects against B. cinerea and the inhibition rates of 2-oxocycloalkylsulfonamides were higher than 2-hydroxycycloalkylsulfonamides, among them. The EC50 values of compounds 3A, 3B(17), 3E, and 4A were 4.21, 4.21 3.24, and 5.29 mu g/mL, respectively. Those compounds containing 5- or 6-membered rings showed better activity than those containing 7-, 8-, or 12-membered rings. Furthermore, the results of the pot culture test showed that almost all of the compounds had effective control activity in vivo and 2-hydroxycycloalkylsulfonamides were obviously superior to 2-oxocycloalkylsulfonamides. The compounds 3E, 4C and 4D presented higher control efficacy than procymidone and pyrimethanil against gray mold disease on cucumber plants.

  DOI：

  10.1021/jf102348x
• 作为产物：
  描述：

  乙烷,三氯氟- 、 2-oxocyclohexylsulfonyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(4-methylphenyl)-2-oxocyclohexylsulfonamide
  参考文献：
  名称：

  Synthesis and biological activities of 2-oxocycloalkylsulfonamides

  摘要：

  A series of novel 2-oxocycloalkylsulfonamides ( 4) were synthesized and their structures confirmed by IR, H-1 NMR, and elemental analysis. The bioassay showed that they have fair to excellent fungicidal activities against Botrytis cinerea Pers and Sclerotinia sclerotiorum. Among them, compounds 4A(10), 4A(11), 4A(12), 4B(2), and 4B(3), the EC50 values of which were 2.12, 3.66, 3.96, 2.38, and 2.43 mu g/mL, respectively, displayed excellent fungicidal activity against B. cinerea Pers, and are comparable with commercial fungicide procymidone ( the EC50 value is 2.45 mu g/mL). 3D QSAR against B. cinerea Pers was studied, a statistically significant and chemically meaningful CoMFA model was developed and some compounds which have a high predicted activity were forecasted. In addition, the bioassay also showed that the compounds have good inhibitory activities against human tumor cells HL-60, BGC-823, Bel-7402 and KB. It is interesting to point out that the antitumor activities of compounds 4 are in accordance with their fungicidal activity to a great extent: compounds having relatively best antitumor activities ( 4A10, 4A11, 4A12, and 4B3) also displayed excellent fungicidal activity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.048

文献信息

• Synthesis and biological activities of 2-oxocycloalkylsulfonamides
  作者：Xinghai Li、Xinling Yang、Xiaomei Liang、Zhenpeng Kai、Huizu Yuan、Dekai Yuan、Jianjun Zhang、Ruiqing Wang、Fuxiang Ran、Shuhua Qi、Yun Ling、Fuheng Chen、Daoquan Wang

  DOI：10.1016/j.bmc.2008.02.048

  日期：2008.4

  A series of novel 2-oxocycloalkylsulfonamides ( 4) were synthesized and their structures confirmed by IR, H-1 NMR, and elemental analysis. The bioassay showed that they have fair to excellent fungicidal activities against Botrytis cinerea Pers and Sclerotinia sclerotiorum. Among them, compounds 4A(10), 4A(11), 4A(12), 4B(2), and 4B(3), the EC50 values of which were 2.12, 3.66, 3.96, 2.38, and 2.43 mu g/mL, respectively, displayed excellent fungicidal activity against B. cinerea Pers, and are comparable with commercial fungicide procymidone ( the EC50 value is 2.45 mu g/mL). 3D QSAR against B. cinerea Pers was studied, a statistically significant and chemically meaningful CoMFA model was developed and some compounds which have a high predicted activity were forecasted. In addition, the bioassay also showed that the compounds have good inhibitory activities against human tumor cells HL-60, BGC-823, Bel-7402 and KB. It is interesting to point out that the antitumor activities of compounds 4 are in accordance with their fungicidal activity to a great extent: compounds having relatively best antitumor activities ( 4A10, 4A11, 4A12, and 4B3) also displayed excellent fungicidal activity. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis, Fungicidal Activity, and Structure−Activity Relationship of 2-Oxo- and 2-Hydroxycycloalkylsulfonamides
  作者：Xing-Hai Li、De-Cai Wu、Zhi-Qiu Qi、Xiu-Wei Li、Zu-Min Gu、Song-Hong Wei、Yang Zhang、Ying-Zi Wang、Ming-Shan Ji

  DOI：10.1021/jf102348x

  日期：2010.11.10

  To explore new potential fungicides, a series of novel compounds, including 11 2-oxocycloalkylsulfonamide (3) and 21 2-hydroxycycloalkylsulfonamide (4) derivatives, were synthesized and their structures were confirmed by H-1 nuclear magnetic resonance (NMR), infrared (IR), and elemental analysis. The results of the bioassay showed that the compounds 3 and 4 possessed excellent fungicidal activity against Botrytis cinerea Pers. both in vitro and in vivo. The fungicidal activity of the compounds with 7- or 8-membered rings is better than those with 5-, 6-, or 12-membered rings. According to the results of the mycelium growth rate test, the EC50 values of the compounds 3C, 4C, 3D, and 40 were 0.80, 0.85, 1.22, and 1.09 mu g/mL, respectively, and similar to or better than commercial fungicide procymidone. The bioassay results of spore germination indicated that most of the compounds exhibited obvious inhibitory effects against B. cinerea and the inhibition rates of 2-oxocycloalkylsulfonamides were higher than 2-hydroxycycloalkylsulfonamides, among them. The EC50 values of compounds 3A, 3B(17), 3E, and 4A were 4.21, 4.21 3.24, and 5.29 mu g/mL, respectively. Those compounds containing 5- or 6-membered rings showed better activity than those containing 7-, 8-, or 12-membered rings. Furthermore, the results of the pot culture test showed that almost all of the compounds had effective control activity in vivo and 2-hydroxycycloalkylsulfonamides were obviously superior to 2-oxocycloalkylsulfonamides. The compounds 3E, 4C and 4D presented higher control efficacy than procymidone and pyrimethanil against gray mold disease on cucumber plants.