5-(4-氯苯基)-2-(三氟甲基)呋喃-3-羧酸 | 175276-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 5-(4-氯苯基)-2-(三氟甲基)呋喃-3-羧酸
• 中文别名: 5-(4-氯苯基)-2-三氟甲基呋喃-3-羧酸
• 英文名称: 5-(4-chlorophenyl)-2-(trifluoromethyl)furan-3-carboxylic acid
• CAS: 175276-60-5
• 化学式: C₁₂H₆ClF₃O₃
• mdl: MFCD00275555
• 分子量: 290.626
• InChiKey: BQUIEVOFWHVZAW-UHFFFAOYSA-N

物化性质

• 熔点：
  188-190°C
• 沸点：
  400.6±45.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi,C
• 危险类别码：
  R36/37/38
• 海关编码：
  2932190090
• 安全说明：
  S22,S26,S36/37/39,S45

反应信息

• 作为反应物：
  描述：

  5-(4-氯苯基)-2-(三氟甲基)呋喃-3-羧酸 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  参考文献：
  名称：

  1,2,4-Triazolsulfone: A novel isosteric replacement of acylsulfonamides in the context of Na V 1.7 inhibition

  摘要：

  Recently, the identification of several classes of aryl sulfonamides and acyl sulfonamides that potently inhibit Na(v)1.7 and demonstrate high levels of selectivity over other Na-v isoforms have been reported. The fully ionizable nature of these inhibitors has been shown to be an important part of the pharmacophore for the observed potency and isoform selectivity. The requirement of this functionality, however, has presented challenges associated with optimization toward inhibitors with drug-like properties and minimal off-target activity. In an effort to obviate these challenges, we set out to develop an orally bioavailable, selective Na(v)1.7 inhibitor, lacking these acidic functional groups. Herein, we report the discovery of a novel series of inhibitors wherein a triazolesulfone has been designed to serve as a bioisostere for the acyl sulfonamide. This work culminated in the delivery of a potent series of inhibitors which demonstrated good levels of selectivity over Na v 1.5 and favorable pharmacokinetics in rodents. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.04.035

文献信息

• Amine Compounds
  申请人：Ohmori Yutaka

  公开号：US20080200535A1

  公开（公告）日：2008-08-21

  There is provided a compound exhibiting an activity of suppressing immune response with reduced adverse drug reactions, which compound is useful in the chemotherapy for preventing or treating, for example, a wide range of various autoimmune diseases including systemic erythematodes, chronic rheumatoid arthritis, Type I diabetes, inflammatory bowel disease, biliary cirrhosis, uveitis, multiple sclerosis or other disorders, or chronic inflammatory diseases, or cancers, lymphoma or leukemia, or resistance to organ or tissue transplantation or rejection against transplantation. Novel amine compounds having an S1P1/Edg1 receptor agonist effect, possible stereoisomers or racemic bodies of the compounds, or pharmacologically acceptable salts, hydrates or solvates of the compound, the stereoisomers or the racemic bodies, or prodrugs of the compounds, the stereoisomers, the racemic bodies, the salts, the hydrates or the solvates, are provided.

  提供了一种化合物，具有抑制免疫反应并减少不良药物反应的活性，该化合物在化疗中用于预防或治疗各种自身免疫性疾病，包括系统性红斑狼疮、慢性类风湿关节炎、I型糖尿病、炎症性肠病、胆汁性肝硬化、葡萄膜炎、多发性硬化或其他疾病，慢性炎症性疾病，癌症，淋巴瘤或白血病，器官或组织移植的抗性或对移植的排斥。提供了具有S1P1/Edg1受体激动剂作用的新型胺类化合物，可能是这些化合物的立体异构体或消旋体，或这些化合物、立体异构体或消旋体的药理学上可接受的盐、水合物或溶剂合物，或这些化合物、立体异构体、消旋体、盐、水合物或溶剂的前药。
• 6-(Aryl-amido or aryl-amidomethyl)-naphthalen-2-yloxy-acidic derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1)
  申请人：Wyeth

  公开号：US20030045560A1

  公开（公告）日：2003-03-06

  This invention provides novel compounds, pharmaceutical compositions and methods of treating thrombotic disorders in mammals, the compounds having the formula: 1 Wherein: Ar is phenyl, naphthyl, furanyl, benzofuranyl, indolyl, pyrazolyl, oxazolyl, fluorenyl, phenylcycloalkane where the cycloalkane can be cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl and Ar can be optionally substituted by 1 to 3 groups selected from C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxy, phenyl-(CH 2 ) 0-6 —, phenyl-(CH 2 ) 0-6 O—, C 3 -C 6 cycloalkyl, —(CH 2 )—C 3 -C 6 cycloalkyl, halogen, C 1 -C 3 perflouroalkyl and C 1 -C 3 perfluoroalkoxy where phenyl can be substituted with from 1 to 3 groups selected from C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenyl, halogen, trifluoromethyl or trifluoromethoxy; R 1 is hydrogen, C 1 -C 6 alkyl or phenyl-(CH 2 ) 1-6 — where phenyl can be substituted with C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo, trifluoromethyl or trifluoromethoxy; R 2 and R 3 are H, C 1 -C 6 alkyl, phenyl-(CH 2 ) 0-3 —, halo and C 1 -C 3 perfluoroalkyl where phenyl can be substituted with C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo, trifluoromethyl or trifluoromethoxy; R 4 is —CHR 5 CO 2 H or —CH 2 -tetrazole where R 5 is H or benzyl; and n=0 or 1; or a pharmaceutically acceptable salt or ester form thereof.

  这项发明提供了新颖的化合物、药物组合物和治疗哺乳动物血栓性疾病的方法，这些化合物具有以下结构式：1其中：Ar为苯基、萘基、呋喃基、苯并呋喃基、吲哚基、吡唑基、噁唑基、芴基、苯基环烷烃，其中环烷烃可以是环丙基、环丁基、环戊基或环己基，Ar可以选择性地被1至3个来自C1-C6烷基、C1-C6烷氧基、羟基、苯基-(CH2)0-6—、苯基-(CH2)0-6O—、C3-C6环烷基、—(CH2)—C3-C6环烷基、卤素、C1-C3全氟烷基和C1-C3全氟烷氧基的基团取代；R1为氢、C1-C6烷基或苯基-(CH2)1-6—，其中苯基可以被C1-C6烷基、C1-C6烷氧基、卤素、三氟甲基或三氟甲氧基取代；R2和R3为H、C1-C6烷基、苯基-(CH2)0-3—、卤素和C1-C3全氟烷基，其中苯基可以被C1-C6烷基、C1-C6烷氧基、卤素、三氟甲基或三氟甲氧基取代；R4为—CHR5CO2H或—CH2-四唑基，其中R5为H或苄基；n=0或1；或其药用可接受的盐或酯形式。
• Carboxamide compounds and their use as antagonists of a human 11cby receptor
  申请人：——

  公开号：US20040063686A1

  公开（公告）日：2004-04-01

  Compounds of formula (I) in which: each A is independently hydrogen, C1-6alkyl optionally substituted by hydroxyl, C1-6alkoxy, C1-6alkenyl or C1-6acyl group or a halogen atom or hydroxyl, CN or CF3 group; R3 is hydrogen, methyl or ethyl; R4 is an optionally substituted aromatic carbocyclic or heterocyclic ring; Z is an O or S atom, or an NH or CH2 group, or a single bond, at the 3 or 4 position of R4 relative to the carbonyl group; R5 is an optionally substituted aromatic carbocyclic or heterocyclic ring, or an optionally substituted, saturated or unsaturated, carbocyclic or heterocyclic ring; and Q is (a) Where X, Y, R1 and R2 are as defined in claim 1; are antagonists of a human 11CBy receptor. 1

  化合物的公式(I)如下：其中：每个A都是独立的氢，C1-6烷基，可选择性地被氢氧基，C1-6氧烷基，C1-6烯基或C1-6酰基或卤素原子或氢氧基，CN或CF3基替代；R3是氢，甲基或乙基；R4是一个可选择性替代的芳香环或杂环；Z是O或S原子，或NH或CH2基，或与羰基相对的R4的3或4位置上的单键；R5是可选择性替代的芳香环或杂环，或可选择性替代的饱和或不饱和的芳香环或杂环；Q是(a)其中X，Y，R1和R2如权利要求1所定义；是人类11CBy受体的拮抗剂。
• [EN] CARBOXAMIDE COMPOUNDS AND THEIR USE AS ANTAGONISTS OF A HUMAN 11CBY RECEPTOR<br/>[FR] COMPOSES DU CARBOXAMIDE ET LEUR UTILISATION COMME ANTAGONISTES D'UN RECEPTEUR 11CBY HUMAIN
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2002010146A1

  公开（公告）日：2002-02-07

  Compounds of formula (I) in which: each A is independently hydrogen, C1-6alkyl optionally substituted by hydroxyl, C1-6alkoxy, C1-6alkenyl or C1-6acyl group or a halogen atom or hydroxyl, CN or CF3 group; R3 is hydrogen, methyl or ethyl; R4 is an optionally substituted aromatic carbocyclic or heterocyclic ring; Z is an O or S atom, or an NH or CH2 group, or a single bond, at the 3 or 4 position of R4 relative to the carbonyl group; R5 is an optionally substituted aromatic carbocyclic or heterocyclic ring, or an optionally substituted, saturated or unsaturated, carbocyclic or heterocyclic ring; and Q is (a) Where X, Y, R1 and R2 are as defined in claim 1; are antagonists of a human 11CBy receptor.

  化合物的公式（I），其中：每个A是独立的氢、C1-6烷基（可选择性地被羟基、C1-6烷氧基、C1-6烯基或C1-6酰基或卤原子或羟基、CN或CF3基替代）、R3是氢、甲基或乙基、R4是可选择性取代的芳香环烃或杂环烃环、Z是O或S原子、或NH或CH2基、或与羰基相对于R4的3或4位置的单键、R5是可选择性取代的芳香环烃或杂环烃环、或可选择性取代的饱和或不饱和的芳香环烃或杂环烃环；Q是（a）式，其中X、Y、R1和R2如权利要求1所定义；是人类11CBy受体的拮抗剂。
• Furan and thiophene derivatives that activate human peroxisome profilerator activated receptors
  申请人：——

  公开号：US20040157890A1

  公开（公告）日：2004-08-12

  A compound of formula (I) or pharmaceutically acceptable salts and solvates thereof, for the treatment of a hPPAR mediated disease or condition. 1

  化合物公式（I）或其药学上可接受的盐和溶剂，用于治疗hPPAR介导的疾病或病况。