4-nitro-5-isopropyl-2-methylphenol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-nitro-5-isopropyl-2-methylphenol
• 英文别名: 5-isopropyl-2-methyl-4-nitrophenol；nitrocarvacrol；4-nitrosocarvacrol；5-Nitro-2-hydroxy-p-cymol；5-Nitro-2-oxy-1-methyl-4-isopropyl-benzol；4-Nitro-carvacrol；NoName_487；2-methyl-4-nitro-5-propan-2-ylphenol
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: RLRCXCWTFYFSHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-nitro-5-isopropyl-2-methylphenol 在 硫化氢 、 氨 作用下， 以 水 为溶剂， 生成 4-氨基-5-异丙基-2-甲基苯酚
  参考文献：
  名称：

  Hybrid molecules of carvacrol and benzoyl urea/thiourea with potential applications in agriculture and medicine

  摘要：

  Benzoyl phenyl urea, a class of insect growth regulator's acts by inhibiting chitin synthesis. Carvacrol, a naturally occurring monoterpenoid is an effective antifungal agent. We have structurally modified carvacrol (2-methyl-5-[1-methylethyl] phenol) by introducing benzoylphenyl urea linkage. Two series of benzoylcarvacryl thiourea (BCTU, 4a-f) and benzoylcarvacryl urea (BCU, 5a-f) derivatives were prepared and characterized by elemental analysis, IR, H-1 and C-13 NMR and Mass spectroscopy. Derivatives 4b, 4d, 4e, 4f and 5d, 5f showed comparable insecticidal activity with the standard BPU lufenuron against Dysdercus koenigii. BCTU derivatives 4c, 4e and BCU 5c showed good antifungal activity against phytopathogenic fungi viz. Magnaporthe grisae, Fusarium oxysporum, Dreschlera oryzae; food spoilage yeasts viz. Debaromyces hansenii, Pichia membranifaciens; and human pathogens viz. Candida albicans and Cryptococcus neoformans. Compounds 5d, 5e and 5f showed potent activity against human pathogens. Moderate and selective activity was observed for other compounds. All the synthesized compounds were non-haemolytic. These compounds have potential application in agriculture and medicine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.017
• 作为产物：
  描述：

  香芹酚 在 硝酸 、 溶剂黄146 作用下， 以33%的产率得到4-nitro-5-isopropyl-2-methylphenol
  参考文献：
  名称：

  香芹酚衍生物作为结核分枝杆菌分支酸突变酶抑制剂的鉴定及其构效关系研究。

  摘要：

  在本研究中，我们确定牛至油的主要酚类成分香芹酚是结核分枝杆菌（MTB）分支酸突变酶（CM）酶的新型小分子抑制剂，IC50为1.06±0.4 µM。使用MTB CM结合的过渡态中间体（PDB：2FP2）的晶体结构作为框架对BITS-Pilani内部数据库进行的虚拟筛选确定了香芹酚为潜在的铅。进一步评估了各种香芹酚衍生物抑制MTB CM酶的能力，全细胞MTB和细胞毒性，以此作为推导结构活性关系（SAR）和优化前导的步骤。

  DOI：

  10.3109/14756366.2013.823958

文献信息

• Identification and structure–activity relationship study of carvacrol derivatives as <i>Mycobacterium tuberculosis</i> chorismate mutase inhibitors
  作者：Reshma Alokam、Variam Ullas Jeankumar、Jonnalagadda Padma Sridevi、Siddharth Sai Matikonda、Santosh Peddi、Mallika Alvala、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.3109/14756366.2013.823958

  日期：2014.8.1

  molecule inhibitor of Mycobacterium tuberculosis (MTB) chorismate mutase (CM) enzyme with IC50 of 1.06 ± 0.4 µM. Virtual screening of the BITS-Pilani in-house database using the crystal structure of the MTB CM bound transition state intermediate (PDB: 2FP2) as framework identified carvacrol as a potential lead. Further various carvacrol derivatives were evaluated in vitro for their ability to inhibit MTB

  在本研究中，我们确定牛至油的主要酚类成分香芹酚是结核分枝杆菌（MTB）分支酸突变酶（CM）酶的新型小分子抑制剂，IC50为1.06±0.4 µM。使用MTB CM结合的过渡态中间体（PDB：2FP2）的晶体结构作为框架对BITS-Pilani内部数据库进行的虚拟筛选确定了香芹酚为潜在的铅。进一步评估了各种香芹酚衍生物抑制MTB CM酶的能力，全细胞MTB和细胞毒性，以此作为推导结构活性关系（SAR）和优化前导的步骤。
• Paterno; Canzoneri, Gazzetta Chimica Italiana, 1878, vol. 8, p. 502
  作者：Paterno、Canzoneri

  DOI：——

  日期：——
• Paterno; Canzoneri, Gazzetta Chimica Italiana, 1880, vol. 10, p. 235
  作者：Paterno、Canzoneri

  DOI：——

  日期：——
• Kehrmann; Schoen, Justus Liebigs Annalen der Chemie, 1900, vol. 310, p. 108
  作者：Kehrmann、Schoen

  DOI：——

  日期：——
• Hybrid molecules of carvacrol and benzoyl urea/thiourea with potential applications in agriculture and medicine
  作者：Umesh D. Pete、Chetan M. Zade、Jitendra D. Bhosale、Santosh G. Tupe、Preeti M. Chaudhary、Amol G. Dikundwar、Ratnamala S. Bendre

  DOI：10.1016/j.bmcl.2012.07.017

  日期：2012.9

  Benzoyl phenyl urea, a class of insect growth regulator's acts by inhibiting chitin synthesis. Carvacrol, a naturally occurring monoterpenoid is an effective antifungal agent. We have structurally modified carvacrol (2-methyl-5-[1-methylethyl] phenol) by introducing benzoylphenyl urea linkage. Two series of benzoylcarvacryl thiourea (BCTU, 4a-f) and benzoylcarvacryl urea (BCU, 5a-f) derivatives were prepared and characterized by elemental analysis, IR, H-1 and C-13 NMR and Mass spectroscopy. Derivatives 4b, 4d, 4e, 4f and 5d, 5f showed comparable insecticidal activity with the standard BPU lufenuron against Dysdercus koenigii. BCTU derivatives 4c, 4e and BCU 5c showed good antifungal activity against phytopathogenic fungi viz. Magnaporthe grisae, Fusarium oxysporum, Dreschlera oryzae; food spoilage yeasts viz. Debaromyces hansenii, Pichia membranifaciens; and human pathogens viz. Candida albicans and Cryptococcus neoformans. Compounds 5d, 5e and 5f showed potent activity against human pathogens. Moderate and selective activity was observed for other compounds. All the synthesized compounds were non-haemolytic. These compounds have potential application in agriculture and medicine. (C) 2012 Elsevier Ltd. All rights reserved.