3-丙氧基-苯胺 | 4469-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-丙氧基-苯胺
• 中文别名: 3-丙氧基苯胺
• 英文名称: 3-propoxyaniline
• 英文别名: 3-Propyloxy-anilin
• CAS: 4469-79-8
• 化学式: C₉H₁₃NO
• mdl: MFCD06801225
• 分子量: 151.208
• InChiKey: VPAHCDXFLUSULH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  3-丙氧基-苯胺 在 selenium(IV) oxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 1-羟基苯并三唑一水物 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 N-(3-Propoxy-phenyl)-N-(1,3,4-trioxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-succinamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Isoquinoline-1,3,4-trione Derivatives as Potent Caspase-3 Inhibitors

  摘要：

  A series of isoquinoline-1,3,4-trione derivatives were identified as novel and potent inhibitors of caspase-3 through structural modification of the original compound from high-throughput screening. Various analogues (2, 6, 9, 13, and 14) were synthesized and identified as caspase inhibitors, and the introduction of a 6-N-acyl group (compound 13) greatly improved their activity. Some of them showed low nanomolar potency against caspase-3 in vitro (for example, for 6k, IC50 = 40 nM) and significant protection against apoptosis in a model cell system. Additionally, compound Of demonstrated a dose-dependent decrease in infarct volume in the transient MCA occlusion stroke model. The present small-molecule caspase-3 inhibitor with novel structures different from structures of known caspase inhibitors revealed a new direction for therapeutic strategies directed against diseases involving abnormally up-regulated apoptosis.

  DOI：

  10.1021/jm050896o
• 作为产物：
  描述：

  间硝基苯酚 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 3-丙氧基-苯胺
  参考文献：
  名称：

  [Cp*RhCl₂]₂-Catalyzed Alkyne Hydroamination to 1,2-Dihydroquinolines

  摘要：

  [Cp*RhCl2](2) catalyzes the formation of 1,2-dihydroquinolines from the reaction of two terminal alkynes and an Aniline. This reaction is believed to proceed via an alkyne hydroamination followed by an alkyne insertion..

  DOI：

  10.1021/om501253v

文献信息

• Studies on antiallergy agents. III. Synthesis of 2-anilino-1,6-dihydro-6-oxo-5-pyrimidinecarboxylic acids and related compounds.
  作者：Kohji OZEKI、Teru ICHIKAWA、Hiroyuki TAKEHARA、Kenjiro TANIMURA、Makoto SATO、Hideya YAGINUMA

  DOI：10.1248/cpb.37.1780

  日期：——

  A series of 2-anilino-1,6-dihydro-6-oxo-5-pyrimidinecarboxylic acids with various substituents was synthesized and evaluated in the rat passive cutaneous anaphylaxis test for antiallergic activity. High activity by intraperitoneal and oral administrations was observed for the 3-trifluoromethyl and 2-alkoxyanilino derivatives (64, 79, 81, 82 and 85). Structure-activity relationships are discussed.

  合成了一系列具有各种取代基的2-苯胺基-1,6-二氢-6-氧代-5-嘧啶羧酸，并在大鼠被动皮肤过敏反应试验中评估了其抗过敏活性。对于3-三氟甲基和2-烷氧基苯胺基衍生物（64、79、81、82和85），观察到腹膜内和口服给药具有高活性。讨论了构效关系。
• Crystallography, quantitative structure-activity relationships, (QSAR) and molecular graphics in a comparative analysis of the inhibition of dihydrofolate reductase from chicken liver and Lactobacillus casei by 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazines
  作者：Corwin Hansch、Bruce A. Hathaway、Zongru Guo、Cynthia Dias Selassie、Stephen W. Dietrich、Jeffrey M. Blaney、Robert Langridge、Karl W. Volz、Bernard T. Kaufman

  DOI：10.1021/jm00368a006

  日期：1984.2

  The inhibition of dihydrofolate reductase from chicken liver and from Lactobacillus casei has been studied with 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazines. It was found that for the chicken enzyme, inhibitor potency for 101 triazines was correlated by the following equation: log 1/Kiapp = 0.85 sigma tau' - 1.04 log (beta X 10 sigma tau' + 1) + 0.57 sigma + 6.36. The parameter

  已经研究了用4，6-二氨基-1，2-二氢-2，2-二甲基-1-（取代的苯基）-s-三嗪对鸡肝和干酪乳杆菌中二氢叶酸还原酶的抑制作用。发现对于鸡肉酶，通过以下方程式关联101种三嗪的抑制剂效能：log 1 / Kiapp = 0.85 sigma tau'-1.04 log（beta X 10 sigma tau'+ 1）+ 0.57 sigma + 6.36。参数tau'表示对于某些取代基，tau =0。就干酪乳杆菌DHFR结果而言，间位和对位导数不能包含在同一方程式中。对于38个间位取代的化合物，发现log 1 / Kiapp = 0.38 tau'3-0.91 log（βX 10 tau'3 + 1）+ 0.71I + 4.60，对于32个对位取代的苯基三嗪log 1 / Kiapp = 0.44 tau'4-0.65 log（βtau'4 + 1'）-0.90 upsilon + 0
• Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides
  作者：Tomas Gonec、Iveta Zadrazilova、Eoghan Nevin、Tereza Kauerova、Matus Pesko、Jiri Kos、Michal Oravec、Peter Kollar、Aidan Coffey、Jim O'Mahony、Alois Cizek、Katarina Kralova、Josef Jampilek

  DOI：10.3390/molecules20069767

  日期：——

  A series of fifteen new N-alkoxyphenylanilides of 3-hydroxynaphthalene-2-carboxylic acid was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra and M. avium subsp. paratuberculosis. Some of the tested compounds showed antibacterial and antimycobacterial activity against the tested strains comparable with or higher than that of the standards ampicillin or rifampicin. 3-Hydroxy-N-(2-propoxyphenyl)naphthalene-2-carboxamide and N-[2-(but-2-yloxy)-phenyl]-3-hydroxynaphthalene-2-carboxamide had MIC = 12 µM against all methicillin-resistant S. aureus strains; thus their activity is 4-fold higher than that of ampicillin. The second mentioned compound as well as 3-hydroxy-N-[3-(prop-2-yloxy)phenyl]-naphthalene-2-carboxamide had MICs = 23 µM and 24 µM against M. tuberculosis respectively. N-[2-(But-2-yloxy)phenyl]-3-hydroxynaphthalene-2-carboxamide demonstrated higher activity against M. avium subsp. paratuberculosis than rifampicin. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using THP-1 cells, and no significant lethal effect was observed for the most potent compounds. The compounds were additionally tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3-Ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 4.5 µM) was the most active PET inhibitor. The structure-activity relationships are discussed.

  制备并表征了一系列15种新的N-烷氧基苯基苯胺衍生物，针对3-羟基萘-2-羧酸。对合成化合物进行的初步体外筛选涉及金黄色葡萄球菌、三种耐甲氧西林金黄色葡萄球菌株、结核分枝杆菌H37Ra和副结核分枝杆菌。部分测试化合物显示出对所测试菌株的抗菌和抗分枝杆菌活性，与标准药物青霉素或利福平相当或更强。3-羟基-N-(2-丙氧基苯基)萘-2-羧酰胺和N-[2-(丁-2-氧基)苯基]-3-羟基萘-2-羧酰胺对所有耐甲氧西林金黄色葡萄球菌株的最低抑制浓度为12 µM，因此它们的活性是青霉素的4倍。第二种提到的化合物以及3-羟基-N-[3-(丙-2-氧基)苯基]-萘-2-羧酰胺对结核分枝杆菌的最低抑制浓度分别为23 µM和24 µM。N-[2-(丁-2-氧基)苯基]-3-羟基萘-2-羧酰胺对副结核分枝杆菌显示出比利福平更高的活性。使用THP-1细胞对最有效的抗分枝杆菌化合物进行的细胞毒性筛选中，观察到大多数有效化合物未表现出显著的致死效应。此外，这些化合物还被测试了其对菠菜(Spinacia oleracea L.) 叶绿体中光合电子传递(PET)的抑制活性。N-(3-乙氧基苯基)-3-羟基萘-2-羧酰胺(半数抑制浓度 = 4.5 µM)是最活跃的PET抑制剂。讨论了结构-活性关系。
• Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides †
  作者：Iva Kapustikova、Andrzej Bak、Tomas Gonec、Jiri Kos、Violetta Kozik、Josef Jampilek

  DOI：10.3390/molecules23071635

  日期：——

  series were investigated in this study. All 57 anilides were analyzed using the reversed-phase high-performance liquid chromatography method for the measurement of lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, a range of software lipophilicity

  对于ADMET量身定制的结构活性模型的合理设计，评估生物活性剂的亲脂特性是必不可少的。N-烷氧基-3-羟基萘-2-甲酰苯胺，N-烷氧基-1-羟基萘-2-甲酰苯胺和N-烷氧基-2-羟基萘-1-甲酰苯胺最近被报道为一系列具有抗分枝杆菌，抗菌素和除草活性。由于发现这些生物活性剂的亲脂性决定了它们的活性，因此在本研究中对这三个系列的亲脂性进行了研究。使用反相高效液相色谱法分析所有57种苯胺类化合物的亲脂性。该过程是在等度条件下，使用封端的非极性C18固定反相色谱柱在甲醇中作为流动相的有机改性剂进行的。在本研究中，使用了一系列亲脂性预测软件来估算一组N-烷氧基苯基羟基萘甲酰胺的clogP值，随后与实验参数进行了交叉比较。因此，将亲脂性（logk）和分布参数（π）的经验值与使用推论亲脂性特征的替代方法计算出的相应计算机特性进行了比较。为了研究衍生物之间的（不相似）相似性，采用了PCA程序以可视化方式观察分子在亲脂性方面的主要性能差异，
• [EN] NEW PIPERIDINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS DE LA PIPÉRIDINE, LEURS COMPOSITIONS PHARMACEUTIQUES ET LEURS UTILISATIONS
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2013092976A1

  公开（公告）日：2013-06-27

  The invention relates to new piperidine derivatives of the formula (I) to their use as medicaments, to methods for their therapeutic use as inhibitors of acetyl-CoA carboxylases and to pharmaceutical compositions containing them.

  该发明涉及新的哌啶衍生物（I）的公式，其用作药物，用作乙酰辅酶A羧化酶抑制剂的治疗用途的方法，以及含有它们的药物组合物。