5H-chromeno[2,3-c]pyridin-5-one | 54629-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5H-chromeno[2,3-c]pyridin-5-one
• 英文别名: 3-aza-9H-xanthen-9-one；2-azaxanthone；3-azaxanthone；chromeno[2,3-c]pyridin-5-one；3-Aza-9-xanthone；chromeno[2,3-c]pyridin-5-one
• CAS: 54629-29-7
• 化学式: C₁₂H₇NO₂
• 分子量: 197.193
• InChiKey: OCUVMSNYNAHWGQ-UHFFFAOYSA-N

物化性质

• 熔点：
  157-158 °C
• 沸点：
  380.6±11.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5H-chromeno[2,3-c]pyridin-5-one 以61%的产率得到
  参考文献：
  名称：

  VILLANI F. J.; MANN T. A.; WEFER E. A.; HANNON J.; LARCA L. L.; LANDON M.+, J. MED. CHEM. , 1975, 18, NO 1, 1-8

  摘要：

  DOI：
• 作为产物：
  描述：

  3-phenoxyisonicotinic acid 在 PPA 作用下， 反应 16.0h， 生成 5H-chromeno[2,3-c]pyridin-5-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

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。
• Intramolecular Anionic Friedel-Crafts Equivalents. A General Regiospecific Route to Substituted and Naturally Occurring Xanthen-9-ones
  作者：O. Familoni、Ileana Ionica、Justin Bower、Victor Snieckus

  DOI：10.1055/s-1997-1533

  日期：1997.9

  An LDA-induced regiospecific and general conversion of diaryl ether 2-carboxamides 4 into substituted xanthones 5, including natural products, 2-hydroxy-1-methoxyxanthone (8) and 6-deoxy-jacareubin (14), is described.

  报道了一种由线性判别分析诱导的、对二芳基醚2-羧酰胺4的区域特异性及普遍性转化，生成取代咕吨酮5，包括天然产物2-羟基-1-甲氧基咕吨酮(8)和6-脱氧雅卡尔宾(14)。
• Synthesis and Evaluation of the Tumor Cell Growth Inhibitory Potential of New Putative HSP90 Inhibitors
  作者：Ana Bizarro、Diana Sousa、Raquel Lima、Loana Musso、Raffaella Cincinelli、Vantina Zuco、Michelandrea De Cesare、Sabrina Dallavalle、M. Vasconcelos

  DOI：10.3390/molecules23020407

  日期：——

  9-diones as inhibitors of HSP90. METHODS In the present work, various compounds with new chromenopyridinone and thiochromenopyridinone scaffolds were synthesized as potential HSP90 inhibitors. Their binding affinity to HSP90 was studied in vitro. Selected compounds (5 and 8) were further studied in various tumor cell lines regarding their potential to cause cell growth inhibition, alter the cell cycle profile

  背景技术热休克蛋白90（HSP90）是癌症治疗的众所周知的靶标。在以前的工作中，我们中的一些人报道了一系列3-芳基萘并[2,3-d]异恶唑-4,9-二酮类化合物作为HSP90的抑制剂。方法在目前的工作中，合成了具有新的色胺吡啶并酮和硫代色吡啶并酮支架的各种化合物作为潜在的HSP90抑制剂。在体外研究了它们对HSP90的结合亲和力。在各种肿瘤细胞系中进一步研究了选定的化合物（5和8），这些化合物可能引起细胞生长抑制，改变细胞周期特征，抑制增殖和诱导凋亡。在两个细胞系中也证实了它们对HSP90客户蛋白质水平的影响。最后，在裸鼠的A431鳞状细胞癌异种移植物中研究了化合物8的抗肿瘤活性。结果我们的结果表明，用化合物5和8处理降低了肿瘤细胞系的增殖，并且化合物8诱导了细胞凋亡。另外，这两种化合物能够下调被称为HSP90“客户”的蛋白质。最后，用化合物5处理异种移植的小鼠导致相当大的剂量依赖性抑制肿
• Tricyclic quinuclidylidenes as potential antihistamine-bronchodilating agents
  作者：Frank J. Villani、Thomas A. Mann、Elizabeth A. Wefer

  DOI：10.1021/jm00241a004

  日期：1975.7
• Internal magnetic field effects on the photochemistry of a xanthone derivate covalently anchored to magnetite nanoparticles
  作者：Mercedes Alvaro、Jose F. Cabeza、Esther Carbonell、Hermenegildo Garcia

  DOI：10.1016/j.cplett.2005.05.069

  日期：2005.7

  Irradiation of azaxanthone in the presence of colloidal magnetite nanoparticles gives rise to the generation of the corresponding azaxanthone triplet, whose lifetime is influenced by internal magnetic field effects. In contrast, covalent tethering between magnetite and azaxanthone promotes photoinduced electron transfer leading to the observation of azaxanthone radical anion. (c) 2005 Elsevier B.V. All rights reserved.