4-苯氧基烟酸 | 54629-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-苯氧基烟酸
• 英文名称: 4-Phenoxy-nicotinsaeure
• 英文别名: 4-phenoxy-nicotinic acid；4-Phenoxypyridine-3-carboxylic acid
• CAS: 54629-95-7
• 化学式: C₁₂H₉NO₃
• mdl: MFCD24072695
• 分子量: 215.208
• InChiKey: QJVUQFFLIRLHBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-苯氧基烟酸 在 PPA 作用下， 反应 16.0h， 生成 1-benzopyrano[3,2-c]pyridin-10-one
  参考文献：
  名称：

  Benzopyranopyridine derivatives. 1. Aminoalkyl derivatives of the azaxanthenes as bronchodilating agents

  摘要：

  The preparation of the four isomeric azaxanthones 3 and a number of their aromatic ring substituted derivatives is described. These ketones were converted into the title compounds which were examined for their biological properties. The most interesting compound in this series, the 1-methyl-4-piperidylidene derivative of 1-azaxanthene, shows the profile of an orally effective potent bronchodilating agent as well as a moderate antihistamine. Biological properties of this compound were compared to a number of antihistamines as well as known bronchodilating agents. Structure-activity relationships are also discussed.

  DOI：

  10.1021/jm00235a001
• 作为产物：
  描述：

  ethyl 4-phenoxynicotinate 在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 4-苯氧基烟酸
  参考文献：
  名称：

  Design, Synthesis, and Antidiabetic Activity of 4-Phenoxynicotinamide and 4-Phenoxypyrimidine-5-carboxamide Derivatives as Potent and Orally Efficacious TGR5 Agonists

  摘要：

  4-Phenoxynicotinamide and 4-phenoxypyrimidine-5-carboxamide derivatives as potent and orally efficacious TGR5 agonists are reported. Several 4-phenoxynicotinamide derivatives were found to activate human and mouse TGR5 (hTGR5 and mTGR5) with EC50 values in the low nanomolar range. Compound 23g, with an EC50 value of 0.72 nM on hTGR5 and an EC50 value of 6.2 nM on mTGR5, was selected for further in vivo efficacy studies. This compound exhibited a significant dose-dependent glucagon-like peptide-1 (GLP-1) secretion effect. A single oral dose of 23g (50 mg/kg) significantly reduced blood glucose levels in db/db mice and caused a 49% reduction in the area under the blood glucose curve (AUC)(0-120) (min) following an oral glucose tolerance test (OGTT) in imprinting control region (ICR) mice. However, 23g stimulated gallbladder filling, which might result in side effects to the gallbladder.

  DOI：

  10.1021/jm301071h

文献信息

• MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-kB ACTIVITY AND USE THEREOF
  申请人：Weinstein David S.

  公开号：US20090075995A1

  公开（公告）日：2009-03-19

  Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity, including inflammatory and immune diseases, having the structure of formula (I): an enantiomer, diastereomer, or tautomer thereof, or a prodrug ester thereof, or a pharmaceutically-acceptable salt thereof, in which: Z is heterocyclo or heteroaryl; A is a 5- to 8-membered carbocyclic ring or a 5- to 8-membered heterocyclic ring; B is a cycloalkyl, cycloalkenyl, aryl, heterocyclo, or heteroaryl ring, wherein each ring is fused to the A ring on adjacent atoms and optionally substituted by one to four groups which are the same or different and are independently selected from R 5 , R 6 , R 7 , and R 8 ; J 1 , J 2 , and J 3 are at each occurrence the same or different and are independently -A 1 QA 2 -; Q is a bond, O, S, S(O), or S(O) 2 ; A 1 and A 2 are the same or different and are at each occurrence independently selected from a bond, C 1-3 alkylene, substituted C 1-3 alkylene, C 2-4 alkenylene, and substituted C 2-4 alkenylene, provided that A 1 and A 2 are chosen so that ring A is a 5- to 8-membered carbocyclic or heterocyclic ring; R 1 to R 11 are as defined herein. Also provided are pharmaceutical compositions and methods of treating inflammatory- or immune-associated diseases and obesity and diabetes employing said compounds.

  提供了一系列新颖的非甾体化合物，这些化合物在治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病中很有用，包括炎性和免疫疾病，具有以下结构式（I）： 其对应的光学异构体、对映异构体或互变异构体，或其前药酯，或其药用可接受盐，其中： Z是杂环或杂芳基； A是一个5至8成员的碳环或一个5至8成员的杂环； B是一个环烷基、环烯基、芳基、杂环或杂芳基环，其中每个环都与A环上的相邻原子融合，并且可以选择性地被一个到四个独立选自R5、R6、R7和R8的相同或不同的组取代； J1、J2和J3每次出现时相同或不同，独立地选自-A1QA2-；Q是键、O、S、S(O)或S(O)2；A1和A2相同或不同，每次出现时独立地选自键、C1-3烷基、取代的C1-3烷基、C2-4烯基和取代的C2-4烯基，前提是A1和A2的选择使得环A是一个5至8成员的碳环或杂环； R1至R11如本文所述定义。 还提供了使用这些化合物的药物组合物和治疗炎性疾病、免疫相关疾病、肥胖和糖尿病的方法。
• [EN] ENHANCERS OF NOTCH SIGNALING AND THEIR USE IN THE TREATMENT OF CANCERS AND MALIGNANCIES MEDICABLE BY UPREGULATION OF NOTCH<br/>[FR] ACTIVATEURS DE SIGNALISATION NOTCH ET LEUR UTILISATION DANS LE TRAITEMENT DE CANCERS ET DE MALIGNITÉS GUÉRISSABLES PAR RÉGULATION À LA HAUSSE DE NOTCH
  申请人：ECOLE POLYTECHNIQUE FÉDÉRALE DE LAUSANNE (EPFL)

  公开号：WO2017158190A1

  公开（公告）日：2017-09-21

  The present invention relates to the use for enhancing Notch signaling in an individual, of a compound showing the general formula (I) and/or a pharmaceutically acceptable salt or ester thereof, for the treatment of a disease selected from the group of dermatological disorders including atopic dermatitis, psoriasis, immune related disorders, cancer, squamous cell carcinoma, cutaneous and lung squamous cell carcinoma, head and neck cancer, non-melanoma skin cancer, basal cell carcinoma and actinic keratosis, neuroendocrine tumors, neuroendocrine small cell carcinoma and carcinoid tumors, thyroid carcinomas, muscular disorders muscular dystrophy and impaired regeneration capacity after injury; use in immunotherapy for cancer.

  本发明涉及使用一种具有通式（I）和/或其药学上可接受的盐或酯的化合物，增强个体中的Notch信号传导，用于治疗选自皮肤病学疾病组的疾病，包括特应性皮炎、银屑病、免疫相关疾病、癌症、鳞状细胞癌、皮肤和肺鳞状细胞癌、头颈癌、非黑色素皮肤癌、基底细胞癌和日光性角化症、神经内分泌肿瘤、神经内分泌小细胞癌和类癌瘤、甲状腺癌、肌肉疾病肌萎缩和损伤后再生能力受损；用于癌症免疫治疗。
• New herbicidal nicotinamide derivatives
  申请人：MAY & BAKER LIMITED

  公开号：EP0053011A1

  公开（公告）日：1982-06-02

  Nicotinamide derivatives of the formula:- (wherein X represents an oxygen or sulphur atom, R1 represents a hydrogen atom or a methyl, ethyl or allyl group, R2 represents a hydrogen, fluorine or chlorine atom, a cyano group or a methyl or ethyl group optionally substituted by one or more fluorine atoms, R3 represents a fluorine, chlorine or bromine atom or a cyano, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy or C1-4 alkanesulphonyl group, one of R4 and R5 represents a hydrogen atom and the other represents a hydrogen, fluorine, chlorine or bromine atom or a cyano, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy or C1-4 alkanesulphonyl group, R6 represents a hydrogen, fluorine or chlorine atom or a cyano or ethynyl group, R7 represents a fluorine or chlorine atom, R8 represents a hydrogen, fluorine, chlorine or bromine atom or a methyl or ethyl group and m represents 0, 1 or 2, with the proviso that when R2 and R6 each represent a hydrogen atom; m represents 0, have been found to possess useful herbicidal properties; herbicidal compositions, methods for controlling the growth of weeds and processes for the preparation of the nicotinamide derivatives are described.

  式中的烟酰胺衍生物：- 其中 X 代表氧原子或硫原子，R1 代表氢原子或甲基、乙基或烯丙基，R2 代表氢原子、氟原子或氯原子、氰基或任选被一个或多个氟原子取代的甲基或乙基、R3 代表氟、氯或溴原子或氰基、三氟甲基、甲氧基、乙氧基、三氟甲氧基或 C1-4 烷磺酰基，R4 和 R5 中的一个代表氢原子，另一个代表氢、R6 代表氢原子、氟原子或氯原子或氰基或乙炔基、R7 代表氟或氯原子，R8 代表氢、氟、氯或溴原子或甲基或乙基，m 代表 0、1 或 2，但当 R2 和 R6 各代表一个氢原子时，m 代表 0；m 代表 0 时，具有有用的除草特性；描述了除草组合物、控制杂草生长的方法和制备烟酰胺衍生物的工艺。
• Enhancers of Notch signaling and the use thereof in the treatment of cancers and malignancies medicable by upregulation of Notch
  申请人：XENIOPRO GmbH

  公开号：US10772876B2

  公开（公告）日：2020-09-15

  The present invention relates to the use for enhancing Notch signaling in an individual, of a compound showing the general formula (I) and/or a pharmaceutically acceptable salt or ester thereof, for the treatment of a disease selected from the group of dermatological disorders including atopic dermatitis, psoriasis, immune related disorders, cancer, squamous cell carcinoma, cutaneous and lung squamous cell carcinoma, head and neck cancer, non-melanoma skin cancer, basal cell carcinoma and actinic keratosis, neuroendocrine tumors, neuroendocrine small cell carcinoma and carcinoid tumors, thyroid carcinomas, muscular disorders muscular dystrophy and impaired regeneration capacity after injury; use in immunotherapy for cancer.

  本发明涉及显示通式(I)的化合物和/或其药学上可接受的盐或酯在个体中增强Notch信号转导的用途，用于治疗选自皮肤病组的疾病，包括特应性皮炎、银屑病、免疫相关疾病、癌症、鳞状细胞癌、皮肤鳞状细胞癌和肺鳞状细胞癌、头颈癌、非黑色素瘤皮肤癌、基底细胞癌和光化性角化病、神经内分泌肿瘤、神经内分泌小细胞癌和类癌、甲状腺癌、肌肉疾病肌肉萎缩症和损伤后再生能力受损；用于癌症免疫疗法。
• VILLANI F. J.; MANN T. A.; WEFER E. A.; HANNON J.; LARCA L. L.; LANDON M.+, J. MED. CHEM. <JMCM-AR>, 1975, 18, NO 1, 1-8
  作者：VILLANI F. J.、 MANN T. A.、 WEFER E. A.、 HANNON J.、 LARCA L. L.、 LANDON M.+

  DOI：——

  日期：——