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

• Targeting Acute Myelogenous Leukemia Using Potent Human Dihydroorotate Dehydrogenase Inhibitors Based on the 2-Hydroxypyrazolo[1,5-<i>a</i>]pyridine Scaffold: SAR of the Aryloxyaryl Moiety
  作者：Stefano Sainas、Marta Giorgis、Paola Circosta、Giulio Poli、Marta Alberti、Alice Passoni、Valentina Gaidano、Agnese C. Pippione、Nicoletta Vitale、Davide Bonanni、Barbara Rolando、Alessandro Cignetti、Cristina Ramondetti、Alessia Lanno、Davide M. Ferraris、Barbara Canepa、Barbara Buccinnà、Marco Piccinini、Menico Rizzi、Giuseppe Saglio、Salam Al-Karadaghi、Donatella Boschi、Riccardo Miggiano、Tiziano Tuccinardi、Marco L. Lolli

  DOI：10.1021/acs.jmedchem.2c00496

  日期：2022.10.13

  In recent years, human dihydroorotate dehydrogenase inhibitors have been associated with acute myelogenous leukemia as well as studied as potent host targeting antivirals. Starting from MEDS433 (IC50 1.2 nM), we kept improving the structure–activity relationship of this class of compounds characterized by 2-hydroxypyrazolo[1,5-a]pyridine scaffold. Using an in silico/crystallography supported design

  近年来，人类二氢乳清酸脱氢酶抑制剂与急性髓性白血病有关，并被研究为有效的靶向抗病毒药物宿主。从MEDS433（IC 50 1.2 nM）开始，我们不断完善这类以2-羟基吡唑并[1,5- a ]吡啶骨架为特征的化合物的构效关系。使用计算机/晶体学支持的设计，我们鉴定了化合物4 (IC 50 7.2 nM)，其特征是存在取代联苯支架的修饰芳氧基芳基部分，对 AML THP1 细胞具有有效的抑制和促分化能力 (EC 50 74 nM)，优于布喹那 (EC 50 249 nM)，与双嘧达莫合用时效果增强。最后，化合物4对非 AML 细胞以及 MEDS433 具有极低的细胞毒性；它在 AML 异种移植小鼠模型中显示出显着的体内抗白血病活性。
• Paterno; Canzoneri, Gazzetta Chimica Italiana, 1878, vol. 8, p. 502
  作者：Paterno、Canzoneri

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  日期：——
• Paterno; Canzoneri, Gazzetta Chimica Italiana, 1880, vol. 10, p. 235
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• Kehrmann; Schoen, Justus Liebigs Annalen der Chemie, 1900, vol. 310, p. 108
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