3-Amino-5-(4-nitro-phenyl)-thiophene-2-carboxylic acid | 187949-93-5

• 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: 3-Amino-5-(4-nitro-phenyl)-thiophene-2-carboxylic acid
• 英文别名: 3-Amino-5-(4-nitrophenyl)-2-thiophenecarboxylic acid；3-amino-5-(4-nitrophenyl)thiophene-2-carboxylic acid
• CAS: 187949-93-5
• 化学式: C₁₁H₈N₂O₄S
• mdl: MFCD09753664
• 分子量: 264.262
• InChiKey: CFTFTFQQYSHMIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  137
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Amino-5-(4-nitro-phenyl)-thiophene-2-carboxylic acid 在 水 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.5h， 生成 3-(3-hexylureido)-5-(4-nitrophenyl)thiophene-2-carboxylic acid
  参考文献：
  名称：

  Structure-Guided Optimization of Small-Molecule Folate Uptake Inhibitors Targeting the Energy-Coupling Factor Transporters

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c02114
• 作为产物：
  描述：

  对硝基苯乙酮 在 sodium methylate 、 potassium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 3-Amino-5-(4-nitro-phenyl)-thiophene-2-carboxylic acid
  参考文献：
  名称：

  Structure-Guided Optimization of Small-Molecule Folate Uptake Inhibitors Targeting the Energy-Coupling Factor Transporters

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c02114

文献信息

• [EN] NEW PYRIMIDONE DERIVATIVES WITH ANTIFUNGAL ACTIVITY<br/>[FR] NOUVEAUX DERIVES PYRIMIDONE A ACTIVITE ANTIFONGIQUE
  申请人：J. URIACH & CIA. S.A.

  公开号：WO1997005130A1

  公开（公告）日：1997-02-13

  (EN) Compounds of general formula (I) and their salts and solvates are antifungal agents and as such are useful in the treatment of various fungal infections. Pharmaceutical compositions including these compounds and processes for their preparation are also provided.(FR) Les composés de la formule générale (I) et leurs sels et solvates sont des agents antifongiques. Il sont utiles pour le traitement de différentes infections fongiques. L'invention concerne également des compositions pharmaceutiques comprenant ces composés et des procédés permettant leur préparation.

  化合物的一般式（I）及其盐和溶剂物是抗真菌剂，因此可用于治疗各种真菌感染。还提供了包括这些化合物的制药组合物和其制备方法。
• Novel small molecule inhibitors targeting the “switch region” of bacterial RNAP: Structure-based optimization of a virtual screening hit
  作者：J. Henning Sahner、Matthias Groh、Matthias Negri、Jörg Haupenthal、Rolf W. Hartmann

  DOI：10.1016/j.ejmech.2013.04.060

  日期：2013.7

  Rising resistance against current antibiotics necessitates the development of antibacterial agents with alternative targets. The "switch region" of RNA polymerase (RNAP), addressed by the myxopyronins, could be such a novel target site. Based on a hit candidate discovered by virtual screening, a small library of 5-phenyl-3-ureidothiophene-2-carboxylic acids was synthesized resulting in compounds with increased RNAP inhibition. Hansch analysis revealed pi (lipophilicity constant) and sigma (Hammet substituent constant) of the substituents at the 5-phenyl moiety to be crucial for activity. The binding mode was proven by the targeted introduction of a moiety mimicking the enecarbamate side chain of myxopyronin into the hit compound, accompanied by enhanced RNAP inhibitory potency. The new compounds displayed good antibacterial activities against Gram positive bacteria and Gram negative Escherichia coli TolC and a reduced resistance frequency compared to the established antibiotic rifampicin. (C) 2013 Elsevier Masson SAS. All rights reserved.
• New Azole Antifungals. 2. Synthesis and Antifungal Activity of Heterocyclecarboxamide Derivatives of 3-Amino-2-aryl-1-azolyl-2-butanol
  作者：Javier Bartroli、Enric Turmo、Mònica Algueró、Eulàlia Boncompte、Maria L. Vericat、Lourdes Conte、Joaquim Ramis、Manuel Merlos、Julián García-Rafanell、Javier Forn

  DOI：10.1021/jm970726e

  日期：1998.5.1

  A series of 92 azole antifungals containing an amido alcohol unit was synthesized. The nature and substitution of the amide portion was systematically modified in search of improved antifungal activity, especially against filamentous fungi. The compounds were tested in vitro against a variety of clinically important pathogens and in vivo (po) in a murine candidosis model. Thiazole and thiophene carboxamides carrying both a substituted phenyl ring and a small alkyl. group were best suited for activity against filamentous fungi. In a subset of these compounds, the amide portion was conformationally locked by means of a pyrimidone ring and it was proven that only an orthogonal orientation of the phenyl ring yields bioactive products. A tendency to display long plasma elimination half-lives was observed in both series. Two compounds, 74 and 107, representative of the open and cyclic amides, respectively, were chosen for further studies, based on their excellent activity in in vivo murine models of candidosis and aspergillosis. This work describes the SARs found within this series. The next paper displays the results obtained in a related series of compounds, the quinazolinones.
• PYRIMIDONE DERIVATIVES WITH ANTIFUNGAL ACTIVITY
  申请人：J. URIACH & CIA. S.A.

  公开号：EP0783501B1

  公开（公告）日：2001-01-10
• NEW PYRIMIDONE DERIVATIVES WITH ANTIFUNGAL ACTIVITY
  申请人：J. URIACH & CIA. S.A.

  公开号：EP0783501A1

  公开（公告）日：1997-07-16