5-(4-tolyl)-thiophene-2-carboxylic acid | 40808-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-(4-tolyl)-thiophene-2-carboxylic acid
• 英文别名: 5-(4-methylphenyl)thiophene-2-carboxylic acid；5-p-tolyl-thiophene-2-carboxylic acid；5-p-Tolyl-thiophen-2-carbonsaeure；2-carboxy-5-(4-methylphenyl)thiophene
• CAS: 40808-21-7
• 化学式: C₁₂H₁₀O₂S
• mdl: MFCD06802425
• 分子量: 218.276
• InChiKey: HAJCITVNZKDTPX-UHFFFAOYSA-N

物化性质

• 熔点：
  217-218 °C
• 沸点：
  399.5±30.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-tolyl)-thiophene-2-carboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  可再生松树树脂松香衍生物在农作物保护中的抗真菌应用

  摘要：

  在当前的工作中，我们从天然产物松香中合成了两个系列的脱氢松香酰胺衍生物，并评估了它们对Valsa mali，Phytophthora capsici，Botrytis cinerea，Sclerotiania sclerotiorum和Fusarium oxysporum的抗真菌作用。体外和体内抗真菌活性结果表明，含噻吩杂环的松香基酰胺化合物对灰葡萄孢的抑制作用更好。尤其是，化合物5b（5-氟-2-噻吩脱氢松香基酰胺）对EC的灰葡萄孢表现出优异的抗真菌性能。50为0.490 mg / L，低于阳性对照戊硫吡py（0.562 mg / L）。生理生化研究表明，化合物5b对灰葡萄孢的主要作用机制是改变菌丝体形态，增加细胞膜通透性，并抑制呼吸代谢中的TCA途径。此外，QSAR和SAR研究表明，松香类酰胺衍生物的电荷分布通过化合物与目标受体之间的氢键键合，结合和静电相互作用，在抗真菌活性中起着关键

  DOI：

  10.1021/acs.jafc.0c00562
• 作为产物：
  描述：

  4-氯-4`-甲基苯丁酮 在 sodium hydroxide 、 硫酸 、 silver(l) oxide 、 三氯氧磷 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 5-(4-tolyl)-thiophene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents

  摘要：

  5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)- thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate acid (5d), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.009

文献信息

• Inhibitors of cathepsin S
  申请人：IRM LLC

  公开号：US20040198780A1

  公开（公告）日：2004-10-07

  The present invention provides compounds, compositions and methods for the selective inhibition of cathepsin S. In a preferred aspect, cathepsin S is selectively inhibited in the presence of at least one other cathepsin isozyme (e.g., cathespin K). The present invention also provides methods for treating a disease state in a subject by selectively inhibiting cathepsin S.

  本发明提供了用于选择性抑制蛋白酶S的化合物、组合物和方法。在一个优选方面，当至少存在另一种蛋白酶同工酶（例如，蛋白酶K）时，选择性地抑制蛋白酶S。本发明还提供了通过选择性抑制蛋白酶S来治疗受试者疾病状态的方法。
• Pharmaceutical compounds
  申请人：Lilly Industries Limited

  公开号：US04983619A1

  公开（公告）日：1991-01-08

  Compounds of the following formula have pharmaceutical properties: ##STR1## in which X is R'(HO)C.dbd.C(CN)--, R.sup.1 (CO)--CH(CN)-- or ##STR2## R.sup.1 and R.sup.2 are each hydrogen or C.sub.1-6 alkyl, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each hydrogen, hydroxy, halogen, nitro, cyano, carboxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, halo-substituted C.sub.1-4 alkyl, halo-substituted C.sub.1-4 alkoxy, halo-substituted C.sub.1-4 alkylthio, C.sub.2-5 alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, R'R"N-- where R' and R" are each hydrogen or C.sub.1-4 alkyl or R'"CONH-- where R'" is C.sub.1-4 alkyl, or a group of the formula --CR.sup.7 R.sup.8 R.sup.9 in which R.sup.7, R.sup.8 and R.sup.9 are each C.sub.1-6 alkyl, halo-substituted C.sub.1-6 alkyl or optionally substituted phenyl, or R.sup.7 and R.sup.8, together with the carbon atom to which they are attached, form a cycloalkyl group containing 3 to 7 carbon atoms, or R.sup.7, R.sup.8 and R.sup.9 together with the carbon atom to which they are attached, form a bicycloalkyl group containing 4 to 9 carbon atoms, and Y is a 5- or 6-membered heterocyclic ring excluding pyrazole; and salts thereof.

  以下化合物具有药理特性：##STR1## 其中X为R'(HO)C.dbd.C(CN)--，R.sup.1 (CO)--CH(CN)--或##STR2## R.sup.1和R.sup.2分别为氢或C.sub.1-6烷基，R.sup.3、R.sup.4、R.sup.5和R.sup.6分别为氢、羟基、卤素、硝基、氰基、羧基、C.sub.1-4烷基、C.sub.1-4烷氧基、C.sub.1-4烷硫基、卤素取代的C.sub.1-4烷基、卤素取代的C.sub.1-4烷氧基、卤素取代的C.sub.1-4烷硫基、C.sub.2-5烷氧羰基、可选择取代的苯基、可选择取代的苯氧基、R'R"N--其中R'和R"分别为氢或C.sub.1-4烷基或R'"CONH--其中R'"为C.sub.1-4烷基，或具有以下式--CR.sup.7 R.sup.8 R.sup.9的基团，其中R.sup.7、R.sup.8和R.sup.9分别为C.sub.1-6烷基、卤素取代的C.sub.1-6烷基或可选择取代的苯基，或R.sup.7和R.sup.8与它们连接的碳原子一起形成含有3至7个碳原子的环烷基，或R.sup.7、R.sup.8和R.sup.9与它们连接的碳原子一起形成含有4至9个碳原子的双环烷基，Y为排除吡唑的5-或6-成员杂环环，以及其盐。
• [EN] THIOPHENE -2- CARBOXYLIC ACID - (1H - BENZIMIDAZOL - 2 YL) - AMIDE DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF THE TEC KINASE ITK (INTERLEUKIN -2- INDUCIBLE T CELL KINASE) FOR THE TREATMENT OF INFLAMMATION, IMMUNOLOGICAL AND ALLERGIC DISORDERS<br/>[FR] DERIVES D'ACIDE THIOPHENE-2-CARBOXYLIQUE (1H-BENZIMIDAZOL-2 YL)-AMIDE ET COMPOSES ASSOCIES UTILISES COMME INHIBITEURS DE LA TEC KINASE ITK (KINASE DES LYMPHOCITES INDUCTIBLES PAR L'INTERLEUKINE -2) POUR TRAITER UNE INFLAMMATION ET DES TROUBLES IMMUNOLOGIQUES ET ALLERGIQUES
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2005079791A1

  公开（公告）日：2005-09-01

  Disclosed are compounds of formula (I): wherein Ar1, Ar2, R1, R2, R3, R4 and Xa are defined herein. The compounds of the invention inhibit Itk kinase and are therefore useful for treating diseases and pathological conditions involving inflammation, immunological disorders and allergic disorders. Also disclosed are processes for preparing these compounds and to pharmaceutical compositions comprising these compounds.

  揭示了式（I）的化合物：其中Ar1、Ar2、R1、R2、R3、R4和Xa在此定义。该发明的化合物抑制Itk激酶，因此对于治疗涉及炎症、免疫紊乱和过敏疾病的疾病和病理状况是有用的。还公开了制备这些化合物的方法以及包含这些化合物的药物组合物。
• Transition-metal-free decarboxylative bromination of aromatic carboxylic acids
  作者：Jacob M. Quibell、Gregory J. P. Perry、Diego M. Cannas、Igor Larrosa

  DOI：10.1039/c8sc01016a

  日期：——

  Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules

  在过去的一个世纪中，将脂肪酸转化为卤代烷的方法取得了显着进展，然而，芳香族酸的类似脱羧溴化仍然是一个长期的挑战。开发有效的芳基溴化物合成方法非常重要，因为它们是合成中的通用试剂，并且存在于许多功能分子中。在此，我们报告了芳香族酸的无过渡金属脱羧溴化反应。该反应适用于许多富含电子的芳族和杂芳族酸，这些酸先前已被证明是Hunsdiecker型反应的不良底物。此外，我们的初步机理研究表明，自由基中间体不参与该反应，这与经典的Hunsdiecker型反应性相反。全面的，
• Design, synthesis and evaluation of novel 5-phenylthiophene derivatives as potent fungicidal of Candida albicans and antifungal reagents of fluconazole-resistant fungi
  作者：Wenbo Yin、Yuxin Zhang、Hengxian Cui、Hong Jiang、Lei Liu、Yang Zheng、Tianxiao Wu、Liyu Zhao、Yin Sun、Xin Su、Song Li、Dongmei Zhao、Maosheng Cheng

  DOI：10.1016/j.ejmech.2021.113740

  日期：2021.12

  5-phenylthiophene derivatives with novel structures were designed and synthesized to combat the increasing incidence of susceptible and drug-resistant fungal infections. The antifungal activity of the synthesized compounds was assessed against seven susceptible strains and six fluconazole-resistant strains. It is especially encouraging that compounds 17b and 17f displayed significant antifungal activities against

  设计和合成了一系列具有新结构的 5-苯基噻吩衍生物，以对抗日益增加的易感和耐药真菌感染的发病率。合成化合物的抗真菌活性针对 7 种敏感菌株和 6 种氟康唑耐药菌株进行了评估。特别令人鼓舞的是，化合物17b和17f对所有测试菌株都显示出显着的抗真菌活性。此外，有效的化合物17b和17f可以防止真菌生物膜的形成，并且17f显示出令人满意的杀菌活性。初步的机理研究表明，化合物17f的强效抗真菌活性源于对白色念珠菌CYP51 的抑制。此外，化合物17b和17f对哺乳动物 A549、MCF-7 和 THLE-2 细胞几乎无毒。这些结果强烈表明化合物17b和17f作为新型抗真菌药物很有前景。