3-[(4-甲酰基)苯基]-5-(4-苯基-5-三氟甲基-2-噻吩基)-1,2,4-恶二唑 | 569685-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-[(4-甲酰基)苯基]-5-(4-苯基-5-三氟甲基-2-噻吩基)-1,2,4-恶二唑
• 英文名称: 3-[(4-formyl)phenyl]-5-(4-phenyl-5-trifluoromethyl-2-thienyl)-1,2,4-oxadiazole
• 英文别名: 4-(5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde；3-[4-(Formyl)phenyl]-5-(4-phenyl-5-trifluoromethyl-2-thienyl)-1,2,4-oxadiazole；4-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]benzaldehyde
• CAS: 569685-42-3
• 化学式: C₂₀H₁₁F₃N₂O₂S
• 分子量: 400.381
• InChiKey: VFHRJAZUOZGYMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-吖丁啶羧酸 、 3-[(4-甲酰基)苯基]-5-(4-苯基-5-三氟甲基-2-噻吩基)-1,2,4-恶二唑 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 1.33h， 以70%的产率得到1-(4-(5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid
  参考文献：
  名称：

  A Rational Utilization of High-Throughput Screening Affords Selective, Orally Bioavailable 1-Benzyl-3-carboxyazetidine Sphingosine-1-phosphate-1 Receptor Agonists

  摘要：

  Moderately potent, selective SIP, receptor agonists identified from high-throughput screening have been adapted into lipophilic tails for a class of orally bioavailable amino acid-based S1P(1) agonists represented by 7. Many of the new compounds are potent S1P(1) agonists that select against the S1P(2), S1P(3), and S1P(4) (although not S1P(5)) receptor subtypes. Analogues 18 and 24 are highly orally bioavailable and possess excellent pharmacokinetic profiles in the rat, dog, and rhesus monkey.

  DOI：

  10.1021/jm0492507
• 作为产物：
  描述：

  1,1,1-三氟-3-苯基丙酮 在 吡啶 、 sodium hydroxide 、 四丙基高钌酸铵 、 草酰氯 、 4 A molecular sieve 、 sodium hydride 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 、 xylene 为溶剂， 反应 45.5h， 生成 3-[(4-甲酰基)苯基]-5-(4-苯基-5-三氟甲基-2-噻吩基)-1,2,4-恶二唑
  参考文献：
  名称：

  A Rational Utilization of High-Throughput Screening Affords Selective, Orally Bioavailable 1-Benzyl-3-carboxyazetidine Sphingosine-1-phosphate-1 Receptor Agonists

  摘要：

  Moderately potent, selective SIP, receptor agonists identified from high-throughput screening have been adapted into lipophilic tails for a class of orally bioavailable amino acid-based S1P(1) agonists represented by 7. Many of the new compounds are potent S1P(1) agonists that select against the S1P(2), S1P(3), and S1P(4) (although not S1P(5)) receptor subtypes. Analogues 18 and 24 are highly orally bioavailable and possess excellent pharmacokinetic profiles in the rat, dog, and rhesus monkey.

  DOI：

  10.1021/jm0492507

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。
• [EN] EDG RECEPTOR AGONISTS<br/>[FR] AGONISTES DU RECEPTEUR EDG
  申请人：MERCK & CO INC

  公开号：WO2003062252A1

  公开（公告）日：2003-07-31

  The present invention encompasses compounds of Formula I: as well as the pharmaceutically acceptable salts and hydrates thereof. The compounds are useful for treating immune mediated diseases and conditions, such as bone marrow, organ and tissue transplant rejection. Pharmaceutical compositions and methods of use are included.

  本发明涵盖式I的化合物：以及其药学上可接受的盐和水合物。该化合物可用于治疗免疫介导的疾病和病状，例如骨髓、器官和组织移植排斥。还包括制药组合物和使用方法。
• N-(benzyl)aminoalkylcarboxylates, phosphinates, phosphonates and tetrazoles as edg receptor agonists
  申请人：Doherty A. George

  公开号：US20050020837A1

  公开（公告）日：2005-01-27

  The present invention encompasses compounds of Formula (I) as well as the pharmaceutically acceptable salts and hydrates thereof. The compounds are useful for treating immune mediated diseases and conditions, such as bone marrow, organ and tissue transplant rejection. Pharmaceutical compositions and methods of use are included.

  本发明涵盖公式（I）的化合物以及其药学上可接受的盐和水合物。该化合物可用于治疗免疫介导的疾病和病况，如骨髓、器官和组织移植排斥反应。包括药物组合物和使用方法。
• Edg receptor agonists
  申请人：Bugianesi L. Robert

  公开号：US20050033055A1

  公开（公告）日：2005-02-10

  The present invention encompasses compounds of Formula 1: as well as the pharmaceutically acceptable salts and hydrates thereof. The compounds are useful for treating immune mediated diseases and conditions, such as bone marrow, organ and tissue transplant rejection. Pharmaceutical compositions and methods of use are included.

  本发明涵盖公式1的化合物，以及其药学上可接受的盐和水合物。这些化合物可用于治疗免疫介导的疾病和病况，例如骨髓、器官和组织移植排斥。还包括制药组合物和使用方法。
• Selective S1P1/Edg1 receptor agonists
  申请人：——

  公开号：US20040058894A1

  公开（公告）日：2004-03-25

  The present invention encompasses a method of treating an immunoregulatory abnormality in a mammalian patient in need of such treatment comprising administering to said patient a compound which is an agonist of the S1P 1 /Edg1 receptor in an amount effective for treating said immunoregulatory abnormality, wherein said compound possesses a selectivity for the S1P1/Edg1 receptor over the S1PR 3 /Edg3 receptor, said compound administered in an amount effective for treating said immunoregulatory abnormality. Pharmaceutical compositions and methods of use are included.

  本发明涵盖了一种治疗哺乳动物患者免疫调节异常的方法，包括向所述患者施用一种化合物，该化合物是S1P1/Edg1受体的激动剂，其剂量足以治疗所述免疫调节异常，其中所述化合物对S1P1/Edg1受体具有选择性，而非S1PR3/Edg3受体，所述化合物的剂量足以治疗所述免疫调节异常。药物组合物和使用方法也包括在内。