4-propylbenzohydrazide | 64328-56-9

• 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: 4-propylbenzohydrazide
• 英文别名: Benzoic acid, 4-propyl-, hydrazide
• CAS: 64328-56-9
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: DSBVDMFDQYWQDE-UHFFFAOYSA-N

物化性质

• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 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

反应信息

• 作为反应物：
  描述：

  4-propylbenzohydrazide 在 indium 、 potassium hydroxide 、 sodium hydroxide 作用下， 生成 2-(prop-2-yn-1-ylthio)-5-(4-propylphenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and Evaluation of Some Substituted Heterocyclic Fluconazole Analogues as Antifungal Agents

  摘要：

  设计、合成了1-(1H-1,2,4-三唑-1-基)-2-(2,4-二氟苯基)-3-4-(取代杂环-1H-1,2,3-三唑-1-基)-2-丙醇(1-10)系列氟康唑类似物，并评价了其抗真菌活性。初步抗真菌测试显示，大多数标题化合物对8种人体致病真菌具有中等活性且谱广，其中化合物1和6对白色念珠菌显示出最佳的抗真菌活性，MIC80值分别达到0.5 μg/mL。

  DOI：

  10.14233/ajchem.2014.15956
• 作为产物：
  描述：

  甲基4-丙基苯甲酸酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 4-propylbenzohydrazide
  参考文献：
  名称：

  Synthesis and Evaluation of Some Substituted Heterocyclic Fluconazole Analogues as Antifungal Agents

  摘要：

  设计、合成了1-(1H-1,2,4-三唑-1-基)-2-(2,4-二氟苯基)-3-4-(取代杂环-1H-1,2,3-三唑-1-基)-2-丙醇(1-10)系列氟康唑类似物，并评价了其抗真菌活性。初步抗真菌测试显示，大多数标题化合物对8种人体致病真菌具有中等活性且谱广，其中化合物1和6对白色念珠菌显示出最佳的抗真菌活性，MIC80值分别达到0.5 μg/mL。

  DOI：

  10.14233/ajchem.2014.15956

文献信息

• Designing and exploring active N′-[(5-nitrofuran-2-yl) methylene] substituted hydrazides against three Trypanosoma cruzi strains more prevalent in Chagas disease patients
  作者：Fanny Palace-Berl、Kerly Fernanda Mesquita Pasqualoto、Salomão Dória Jorge、Bianca Zingales、Rodrigo Rocha Zorzi、Marcelo Nunes Silva、Adilson Kleber Ferreira、Ricardo Alexandre de Azevedo、Sarah Fernandes Teixeira、Leoberto Costa Tavares

  DOI：10.1016/j.ejmech.2015.03.066

  日期：2015.5

  Chagas disease affects around 8 million people worldwide and its treatment depends on only two nitroheterocyclic drugs, benznidazole (BZD) and nifurtimox (NFX). Both drugs have limited curative power in chronic phase of disease. Nifuroxazide (NF), a nitroheterocyclic drug, was used as lead to design a set of twenty one compounds in order to improve the anti-Trypanosoma cruzi activity. Lipinski's rules were considered in order to support drug-likeness designing. The set of N'-[(5-nitrofuran-2-yl) methylene] substituted hydrazides was assayed against three T. cruzi strains, which represent the discrete typing units more prevalent in human patients: Y (TcII), Silvio X10 cl1 (TcI), and Bug 2149 cl10 (TcV). All the derivatives, except one, showed enhanced trypanocidal activity against the three strains as compared to BZD. In the Y strain 62% of the compounds were more active than NFX. The most active compound was N'((5-nitrofuran-2-yl) methylene)biphenyl-4-carbohydrazide (C20), which showed IC50 values of 1.17 +/- 0.12 mu M; 3.17 +/- 0.32 mu M; and 1.81 +/- 0.18 mu M for Y, Silvio X10 cl1, and Bug 2149 cl10 strains, respectively. Cytotoxicity assays with human fibroblast cells have demonstrated high selectivity indices for several compounds. Exploratory data analysis indicated that primarily topological, steric/geometric, and electronic properties have contributed to the discrimination of the set of investigated compounds. The findings can be helpful to drive the designing, and subsequently, the synthesis of additional promising drugs against Chagas disease. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Ligand-based design, synthesis, and experimental evaluation of novel benzofuroxan derivatives as anti-Trypanosoma cruzi agents
  作者：Salomão Dória Jorge、Fanny Palace-Berl、Kerly Fernanda Mesquita Pasqualoto、Marina Ishii、Adilson Kleber Ferreira、Carolina Maria Berra、Rosemary Viola Bosch、Durvanei Augusto Maria、Leoberto Costa Tavares

  DOI：10.1016/j.ejmech.2013.03.053

  日期：2013.6

  A set of substituted-[N'-(benzofuroxan-5-yl)methylene]benzohydrazides (4a-t), previously designed and synthesized, was experimentally assayed against Trypanosoma cruzi, the etiological agent of Chagas' disease, one of the most neglected tropical diseases. Exploratory data analysis, Hansch approach and VolSurf formalism were applied to aid the ligand-based design of novel anti-T cruzi agents. The best 2D-QSAR model showed suitable statistical measures [n = 18; s = 0.11; F = 42.19; R-2 = 0.90 and Q(2) = 0.77 (SDEP = 0.15)], and according to the optimum 3D-QSAR model [R-2 = 0.98, Q(2) = 0.93 (SDEP = 0.08)], three latent variables explained 62% of the total variance from original data. Steric and hydrophobic properties were pointed out as the key for biological activity. Based upon the findings, six novel benzofuroxan derivatives (4u-z) were designed, synthesized, and in vitro assayed to perform the QSAR external prediction. Then, the predictability for the both models, 2D-QSAR (R-pred(2) = 0.91) and 3D-QSAR (R-pred(2) = 0.77), was experimentally validated, and compound 4u was identified as the most active anti-T. cruzi hit (IC50 = 3.04 mu M). (C) 2013 Elsevier Masson SAS. All rights reserved.
• A new class of nifuroxazide analogues: Synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus
  作者：Andrea Masunari、Leoberto Costa Tavares

  DOI：10.1016/j.bmc.2007.03.068

  日期：2007.6

  Hospital-acquired methicillin-resistant Staphylococcus aureus (MRSA) has been an increasing problem worldwide since the initial reports over 40 years ago. To examine new drug leads with potential antibacterial activities, 14 p-substituted benzoic acid [(5-nitro-thiophen-2-yl)-methylene]-hydrazides were designed, synthesized, and tested against standard and multidrug-resistant S. aureus strains by serial dilution tests. All compounds exhibited significant bacteriostatic activity and some of them also showed bactericidal activity. The results confirmed the potential of this class of compounds as an alternative for the development of selective antimicrobial agents. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis, molecular modeling and preliminary biological evaluation of a set of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole as potential antibacterial, anti-Trypanosoma cruzi and antifungal agents
  作者：Marina Ishii、Salomão Dória Jorge、Alex Alfredo de Oliveira、Fanny Palace-Berl、Ieda Yuriko Sonehara、Kerly Fernanda Mesquita Pasqualoto、Leoberto Costa Tavares

  DOI：10.1016/j.bmc.2011.09.009

  日期：2011.11

  A series of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives was synthesized and their activity screened in vitro against Staphylococcus aureus, Trypanosoma cruzi, and Candida albicans. The bioactivity was expressed as minimum inhibitory concentration (MIC) for S. aureus strains, and as fifty-percent inhibitory concentration (IC50) of parasite population growth for T. cruzi. A molecular modeling approach was performed to establish qualitative relationships regarding the biological data and the compounds' physicochemical properties. The 5-(4-OC4H9Ph, 5l), and 5-(4-CO2CH3Ph, 5o) derivatives were the most active compounds for S. aureus ATCC 25923 (MIC = 1.95 - 1.25 mu g/mL) and T. cruzi (IC50 = 7.91 mu M), respectively. Also, a preliminary evaluation against C. albicans involving some compounds was performed and the 5-(4-CH3Ph, 5e) derivative was the most active compound (MIC = 3.28-2.95 mu g/mL). In this preliminary study, all synthesized 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives were active against all microorganisms tested. (C) 2011 Elsevier Ltd. All rights reserved.
• Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: 1,3,4-Thiadiazolylmethylphenyl glucoside congeners
  作者：Junwon Lee、Sung-Han Lee、Hee Jeong Seo、Eun-Jung Son、Suk Ho Lee、Myung Eun Jung、MinWoo Lee、Ho-Kyun Han、Jeongmin Kim、Jahyo Kang、Jinhwa Lee

  DOI：10.1016/j.bmc.2010.01.073

  日期：2010.3

  Novel C-aryl glucoside SGLT2 inhibitors containing 1,3,4-thiadiazole moieties were designed and synthesized. Among the compounds tested, biaryl-type compounds containing pyrazine 59, 2-furan 61, and 3-thiophene 71 showed the best in vitro inhibitory activities to date (IC50 = 3.51-7.03 nM) against SGLT2. A selected compound 61, demonstrated reasonable blood glucose-lowering effects, indicating that the information obtained from the SAR studies in this 1,3,4-thiadiazolylmethylphenyl glucoside series might help to design more active SGLT2 inhibitors that are structurally related. (C) 2010 Elsevier Ltd. All rights reserved.