4-异丙基苯甲酰肼 | 5351-24-6

• 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
• 中文名称: 4-异丙基苯甲酰肼
• 中文别名: 4-异丙基苯甲酸肼
• 英文名称: 4-isopropylbenzoic acid hydrazide
• 英文别名: 4-isopropylbenzohydrazide；4-propan-2-ylbenzohydrazide
• CAS: 5351-24-6
• 化学式: C₁₀H₁₄N₂O
• mdl: MFCD00850766
• 分子量: 178.234
• InChiKey: ZRVXDEFJKAAGGH-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  4-异丙基苯甲酰肼 在 sodium ethanolate 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-(4-Isopropylphenyl)-5-((2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)thio)-1,3,4-oxadiazole
  参考文献：
  名称：

  Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents

  摘要：

  A series of novel 1,3,4-oxadiazole thioether derivatives (compounds 9-44) were designed and synthesized as potential inhibitors of thymidylate synthase (TS) and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 18 bearing a nitro substituent exhibited more potent in vitro anticancer activities with IC50 values of 0.7 +/- 0.2, 30.0 +/- 1.2, 18.3 +/- 1.4 mu M, respectively, which was superior to the positive control. In the further study, it was identified as the most potent inhibitor against two kinds of TS protein (for human TS and Escherichia coli TS, IC50 values: 0.62 and 0.47 mu M, respectively) in the TS inhibition assay in vitro and the most potent antibacterial agents with MIC (minimum inhibitory concentrations) of 1.56-3.13 mu g/mL against the tested four bacterial strains. Molecular docking and 3D-QSAR study supported that compound 18 can be selected as dual antitumor/antibacterial candidate in the future study. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.008
• 作为产物：
  描述：

  4-异丙基苯甲酸 在 草酰氯 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 4-异丙基苯甲酰肼
  参考文献：
  名称：

  Essential Oil-Based Design and Development of Novel Anti-Candida Azoles Formulation

  摘要：

  Candida是最常见的真菌类，会引起人类表浅和侵袭性疾病。虽然白念珠菌是人类真菌感染最常见的原因，但C. auris是一种新兴的严重病原体，引起的并发症类似于白念珠菌。白念珠菌和C. auris都与高死亡率相关，主要是因为它们对大多数可用抗真菌药物表现出多药耐药性。尽管设计了几种针对白念珠菌的化合物，但很少或没有对C. auris进行测试。因此，迫切需要开发新型有效的抗真菌药物，不仅可以适应白念珠菌，还可以适应其他念珠菌种，特别是新兴种，包括C. auris。受精油香茴醛的显著广谱抗真菌活性和已报道的氮唑类药物在抗真菌药物中的广泛应用的启发，设计和开发了一系列化合物（UoST1-11）。新化合物的设计旨在克服香茴醛醛基的毒性，并从氮唑类药物的抗真菌选择性中获益。新开发的UoST化合物显示出显著的抗念珠菌活性，对两种念珠菌种都有效。最佳候选化合物UoST5进一步制成聚合物纳米颗粒（NPs）。新配方UoST5-NPs显示出与无纳米颗粒药物相似的活性，同时在24小时后仅释放25％，保持长效活性长达48小时，并不产生毒性。总之，开发了新的氮唑类配方，对白念珠菌和C. auris的活性显著增强，同时在较低浓度下保持长效作用且无毒性。

  DOI：

  10.3390/molecules25061463

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：UCL BUSINESS LTD

  公开号：WO2020043866A1

  公开（公告）日：2020-03-05

  A compound for use in the treatment of a disease ameliorated by the inhibition of Notum of formula (I): (I)

  一种用于治疗通过抑制公式（I）中的Notum改善的疾病的化合物：（I）
• Essential Oil-Based Design and Development of Novel Anti-Candida Azoles Formulation
  作者：Rania Hamdy、Bahgat Fayed、Alshaimaa M. Hamoda、Mutasem Rawas-Qalaji、Mohamed Haider、Sameh S. M. Soliman

  DOI：10.3390/molecules25061463

  日期：——

  Candida is the most common fungal class, causing both superficial and invasive diseases in humans. Although Candida albicans is the most common cause of fungal infections in humans, C. auris is a new emergent serious pathogen causing complications similar to those of C. albicans. Both C. albicans and C. auris are associated with high mortality rates, mainly because of their multidrug-resistance patterns against most available antifungal drugs. Although several compounds were designed against C. albicans, very few or none were tested on C. auris. Therefore, it is urgent to develop novel effective antifungal drugs that can accommodate not only C. albicans, but also other Candida spp., particularly newly emergent one, including C. auris. Inspired by the significant broad-spectrum antifungal activities of the essential oil cuminaldehyde and the reported wide incorporation of azoles in the antifungal drugs, a series of compounds (UoST1-11) was designed and developed. The new compounds were designed to overcome the toxicity of the aldehyde group of cuminaldehyde and benefit from the antifungal selectivity of azoles. The new developed UoST compounds showed significant anti-Candida activities against both Candida species. The best candidate compound, UoST5, was further formulated into polymeric nanoparticles (NPs). The new formula, UoST5-NPs, showed similar activities to the nanoparticles-free drug, while providing only 25% release after 24 h, maintainng prolonged activity up to 48 h and affording no toxicity. In conclusion, new azole formulations with significantly enhanced activities against C. albicans and C. auris, while maintaining prolonged action and no toxicities at lower concentrations, were developed.

  Candida是最常见的真菌类，会引起人类表浅和侵袭性疾病。虽然白念珠菌是人类真菌感染最常见的原因，但C. auris是一种新兴的严重病原体，引起的并发症类似于白念珠菌。白念珠菌和C. auris都与高死亡率相关，主要是因为它们对大多数可用抗真菌药物表现出多药耐药性。尽管设计了几种针对白念珠菌的化合物，但很少或没有对C. auris进行测试。因此，迫切需要开发新型有效的抗真菌药物，不仅可以适应白念珠菌，还可以适应其他念珠菌种，特别是新兴种，包括C. auris。受精油香茴醛的显著广谱抗真菌活性和已报道的氮唑类药物在抗真菌药物中的广泛应用的启发，设计和开发了一系列化合物（UoST1-11）。新化合物的设计旨在克服香茴醛醛基的毒性，并从氮唑类药物的抗真菌选择性中获益。新开发的UoST化合物显示出显著的抗念珠菌活性，对两种念珠菌种都有效。最佳候选化合物UoST5进一步制成聚合物纳米颗粒（NPs）。新配方UoST5-NPs显示出与无纳米颗粒药物相似的活性，同时在24小时后仅释放25％，保持长效活性长达48小时，并不产生毒性。总之，开发了新的氮唑类配方，对白念珠菌和C. auris的活性显著增强，同时在较低浓度下保持长效作用且无毒性。
• Synthesis, molecular modeling and biological evaluation of 2-(benzylthio)-5-aryloxadiazole derivatives as anti-tumor agents
  作者：Kai Liu、Xiang Lu、Hong-Jia Zhang、Juan Sun、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2011.11.015

  日期：2012.1

  A series of 2-(benzylthio)-5-aryloxadiazole derivatives have been designed and synthesized, and their biological activities are also evaluated for EGFR inhibitory activity. Fourteen compounds among the twenty compounds are reported for the first time. Their chemical structures are characterized by 1H NMR, MS, and elemental analysis. Anti-proliferative and EGFR inhibition assay results have demonstrated

  已经设计和合成了一系列2-（苄硫基）-5-芳基恶二唑衍生物，并且还评估了它们的生物活性对EGFR的抑制活性。首次报道了二十种化合物中的十四种化合物。它们的化学结构通过1 H NMR，MS和元素分析进行表征。抗增殖和EGFR抑制测定的结果已经证实，化合物3e中示出了最有效的生物活性（IC 50  = 1.09μM为MCF-7和IC 50  = 1.51μM为EGFR）。已执行对接仿真以定位化合物3e进入EGFR活性位点以确定可能的结合模型，估计结合自由能值为-10.7 kcal / mol。在肿瘤生长抑制中具有有效抑制活性的化合物3e可能是有前途的抗肿瘤主导化合物，值得进一步研究。
• Selective inhibition of <i>Rhizopus</i> eumelanin biosynthesis by novel natural product scaffold-based designs caused significant inhibition of fungal pathogenesis
  作者：Sameh S. M. Soliman、Rania Hamdy、Samia A. Elseginy、Teclegiorgis Gebremariam、Alshaimaa M. Hamoda、Mohamed Madkour、Thenmozhi Venkatachalam、Mai N. Ershaid、Mohammad G. Mohammad、Georgios Chamilos、Ashraf S. Ibrahim

  DOI：10.1042/bcj20200310

  日期：2020.7.17

  naturally in most living organisms. Fungal melanin is a major putative virulence factor of Mucorales fungi that allows intracellular persistence by inducing phagosome maturation arrest. Recently, it has been shown that the black pigments of Rhizopus delemar is of eumelanin type, that requires the involvement of tyrosinase (a copper-dependent enzyme) in its biosynthesis. Herein, we have developed a series

  黑色素是在大多数生物体中自然合成的深色色素。真菌黑色素是毛霉菌属真菌的主要假定毒力因子，通过诱导吞噬体成熟阻滞允许细胞内持续存在。最近，已经表明，Rhizopus delemar 的黑色色素属于真黑素类型，这需要酪氨酸酶（一种依赖铜的酶）参与其生物合成。在此，我们开发了一系列化合物 (UOSC-1-14) 来选择性靶向根霉黑色素，并在治疗上探索了这种机制。这些化合物是基于从植物来源鉴定的天然产物孜然醛的支架设计的，并已显示出对黑色素生成的非选择性抑制。虽然所有合成的化合物都显示出对根霉黑色素产生的显着抑制和对哺乳动物细胞的有限毒性，但基于它们对真菌黑色素的选择性抑制，只有四种化合物（UOSC-1、2、13 和 14）被选为有前景的候选物。化合物UOSC-2的活性与阳性对照曲酸相当。选定的候选物通过靶向真菌酪氨酸酶显示出对根霉黑色素的显着抑制，但对人黑色素没有显着抑制作用，IC50 比参考标准曲酸低
• TREATMENT AND PREVENTION OF NEUROPATHIC PAIN WITH P2Y14 ANTAGONISTS
  申请人：Saint Louis University

  公开号：US20210024489A1

  公开（公告）日：2021-01-28

  Disclosed herein are methods for treating neuropathic pain in a subject in need thereof. The methods include: administering to a subject in need thereof a therapeutically effective amount of an antagonist of P2Y14.

  本文公开了治疗神经病理性疼痛的方法，包括向需要的受试者施用P2Y14的拮抗剂的治疗有效量。