2-(4-氟苯基)-4-甲基噻唑-5-羧酸 | 144060-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-氟苯基)-4-甲基噻唑-5-羧酸
• 中文别名: 噻唑,2-(4-氟苯基)-4-甲基-；2-(4-氟苯基)-4-甲基-5-噻唑羧酸
• 英文名称: 2-(4-fluorophenyl)-4-methyl-1,3-thiazole-5-carboxylic acid
• 英文别名: 4-methyl-2-(4-fluorophenyl)thiazole-5-carboxylic acid
• CAS: 144060-99-1
• 化学式: C₁₁H₈FNO₂S
• mdl: MFCD06857923
• 分子量: 237.254
• InChiKey: LPBSLIRPWIFCQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934100090
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-(4-氟苯基)-4-甲基噻唑-5-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-methyl-2-(4-fluorophenyl)thiazole-5-carbonyl chloride
  参考文献：
  名称：

  作为 VEGFR-2/c-Met 双重抑制剂的 4-苯氧基-吡啶/嘧啶衍生物的设计、合成和生物学评价

  摘要：

  设计、合成和评估了一类 4-苯氧基-吡啶/嘧啶衍生物（23a-23p和24a-24h ）作为有效的双重 VEGFR-2/c-Met 抑制剂。化合物的体外抗癌细胞增殖活性表明化合物23k被认为是一种有前途的衍生物。与先导化合物 Foretinib 和 Sorafenib 相比，23k对 A549、MCF-7、HepG2 和 Ovcar-3 细胞系表现出优异的抑制活性，IC 50值为 2.16 ± 0.19 μM、9.13 ± 0.65 μM、20.15 ± 2.64 和 9.65 ±分别为 0.51 μM。此外，23k对人类正常细胞（LO2 细胞）表现出低毒性，IC 50值高于 100 μM。在激酶测定中，最有希望的化合物23k显示出优异的激酶抑制活性和对 VEGFR-2 和 c-Met 的选择性，IC 50值分别为 1.05 和 1.43 μM。进一步的活性​​研究表明，23k不仅诱导 A549

  DOI：

  10.1039/d2nj01561g
• 作为产物：
  描述：

  ethyl 2-(4-fluorophenyl)-4-methylthiazole-5-carboxylate 在 sodium hydroxide 作用下， 生成 2-(4-氟苯基)-4-甲基噻唑-5-羧酸
  参考文献：
  名称：

  Microwave Assisted Synthesis and Antibacterial Activity of New 1,3,4-Thiadiazoles and 1,2,4-Triazoles Derived from 2-{2-[2-(4-Fluorophenyl)-4-methylthiazol-5-yl]-1H-benzo[d]imidazol-1-yl}acetohydrazide

  摘要：

  A series of novel derivatives of 1-(2-{2-[2-(4-fluorophenyl)-4-methylthiazol-5-yl]-1H-benzo[d]imidazol-1-yl}acetyl)-4-phenylthiosemicarbazide, 5-({2-[2-(4-fluorophenyl)-4-methylthiazol-5-yl]-1H-benzo[d]imidazol-1-yl}methyl)-4-phenyl-4H-1,2,4-triazole-3-thiol and 5-({2-[2-(4-fluorophenyl)-4-methylthiazol-5-yl]-1H-benzo[d]imidazol-1-yl}methyl)-N-phenyl-1,3,4-thiadiazol-2-amine have been synthesized by the conventional method as well as using MW irradiation. All newly synthesized compounds have been tested for antibacterial activity. Several products have demonstrated moderate activity against gram positive and gram negative bacterial strains.

  DOI：

  10.1134/s1070363220090200

文献信息

• HETEROCYCLIC COMPOUND AND p27Kip1 DEGRADATION INHIBITOR
  申请人：Uchida Hiroshi

  公开号：US20130079306A1

  公开（公告）日：2013-03-28

  A novel heterocyclic compound or a salt thereof useful for selectively inhibiting the degradation of p27 Kip1 is provided. The compound or the salt thereof is represented by the following formula (1): wherein A represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, the group A may have a substituent; the ring B represents a 5- to 8-membered monocyclic heterocyclic ring or a condensed ring containing the monocyclic heterocyclic ring, the ring B may have a substituent; the ring C represents an aromatic ring, the ring C may have a substituent; L represents a linker comprising a main chain having 3 to 5 atoms selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom and a sulfur atom, wherein at least one atom in the main chain is a hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, the linker L may have a substituent; and n is 0 or 1.

  提供了一种新型杂环化合物或其盐，用于选择性地抑制p27Kip1的降解。该化合物或其盐由以下式（1）表示：其中A代表烷基、环烷基、芳基或杂环基，基团A可能有取代基；环B代表5至8成员的单环杂环环或包含该单环杂环环的缩合环，环B可能有取代基；环C代表芳香环，环C可能有取代基；L代表包含3至5个原子的主链的连接物，所述原子选自碳原子、氮原子、氧原子和硫原子组成的群，其中主链中的至少一个原子是选自氮原子、氧原子和硫原子组成的杂原子，连接物L可能有取代基；n为0或1。
• [EN] NOVEL COMPOUND, METHOD FOR PREPARATION THEREOF, AND ANTIFUNGAL COMPOSITION COMPRISING THE SAME<br/>[FR] NOUVEAU COMPOSÉ, PROCÉDÉ DE PRÉPARATION DE CELUI-CI, ET COMPOSITION ANTIFONGIQUE LE COMPRENANT
  申请人：DAE WOONG PHARMA

  公开号：WO2015069011A1

  公开（公告）日：2015-05-14

  Disclosed are a compound having an excellent antifungal activity, a composition containing the same, and its use for prevention and treatment of fungal infectious diseases.

  揭示了一种具有优异抗真菌活性的化合物，以及包含该化合物的组合物，以及其用于预防和治疗真菌感染性疾病的用途。
• 噻唑-5-甲酰胺化合物、及其制法和药物组合物 与用途
  申请人：中国医学科学院药物研究所

  公开号：CN102532123B

  公开（公告）日：2016-03-09

  本发明涉及通式I的新的2-苯基噻唑-5-甲酰胺化合物、其前体、立体异构体和生理上可接受的盐、含有所述化合物的药物组合物以及在医药方面的应用。
• Discovery of cyclic amine-substituted benzoic acids as PPARα agonists
  作者：Masahiro Nomura、Kazuhiro Yumoto、Takehiro Shinozaki、Shigeki Isogai、Yasuo Takano、Koji Murakami

  DOI：10.1016/j.bmcl.2011.11.002

  日期：2012.1

  A series of novel cyclic amine-substituted benzoic acid derivatives were synthesized and evaluated for their PPAR alpha agonist activity. Strucure-activity relationship studies led to the identification of (S)-3-[3[2-(4-chlorophenyl)-4-methylthyazole-5-carboxamido] piperidin-1-yl] benzoic acid (S)-4f (KRP-105) as a potent and high subtype-selective human PPARa agonist. (S)-4f showed excellent PK profile and oral administration of (S)-4f to high-fat diet dogs effectively lowered triglycerides. (C) 2011 Elsevier Ltd. All rights reserved.
• Substituted 2-[(4-Aminomethyl)phenoxy]-2-methylpropionic Acid PPARα Agonists. 1. Discovery of a Novel Series of Potent HDLc Raising Agents
  作者：Michael L. Sierra、Véronique Beneton、Anne-Bénédict Boullay、Thierry Boyer、Andrew G. Brewster、Frédéric Donche、Marie-Claire Forest、Marie-Hélène Fouchet、Françoise J. Gellibert、Didier A. Grillot、Millard H. Lambert、Alain Laroze、Christelle Le Grumelec、Jean Michel Linget、Valerie G. Montana、Van-Loc Nguyen、Edwige Nicodème、Vipul Patel、Annie Penfornis、Olivier Pineau、Danig Pohin、Florent Potvain、Géraldine Poulain、Cécile Bertho Ruault、Michael Saunders、Jérôme Toum、H. Eric Xu、Robert X. Xu、Pascal M. Pianetti

  DOI：10.1021/jm058056x

  日期：2007.2.1

  The peroxisome proliferator activated receptors PPAR alpha, PPAR gamma, and PPAR delta are ligand-activated transcription factors that play a key role in lipid homeostasis. The fibrates raise circulating levels of high-density lipoprotein cholesterol and lower levels of triglycerides in part through their activity as PPAR alpha agonists; however, the low potency and restricted selectivity of the fibrates may limit their efficacy, and it would be desirable to develop more potent and selective PPAR alpha agonists. Modification of the selective PPAR delta agonist 1 (GW501516) so as to incorporate the 2-aryl-2-methylpropionic acid group of the fibrates led to a marked shift in potency and selectivity toward PPAR alpha agonism. Optimization of the series gave 25a, which shows EC50 = 4 nM on PPAR alpha and at least 500-fold selectivity versus PPAR delta and PPAR gamma. Compound 25a (GW590735) has been progressed to clinical trials for the treatment of diseases of lipid imbalance.