[8-amino-2-(5-bromo-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-(3-methyl-piperidin-1-yl)-methanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: [8-amino-2-(5-bromo-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-(3-methyl-piperidin-1-yl)-methanone
• 英文别名: [8-amino-2-(5-bromofuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-(3-methylpiperidin-1-yl)methanone
• 化学式: C₁₇H₁₈BrN₅O₂
• 分子量: 404.266
• InChiKey: CTENSBDICWZOOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-溴-2-呋喃甲醛 在 N-羟基-2,4,6-三甲基苯磺酰胺 、 三甲基铝 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 80.0h， 生成 [8-amino-2-(5-bromo-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-(3-methyl-piperidin-1-yl)-methanone
  参考文献：
  名称：

  比较异构体三唑并吡啶衍生物对腺苷受体亚型的抑制活性或相似结构是否显示出相似的生物活性？

  摘要：

  首次描述了一系列8-氨基-2-芳基-[1,2,4]三唑并[1,5-a]吡啶-6-羧基酰胺衍生物的合成。将20种衍生物的一部分与它们的同分异构的5-氨基-2-芳基-[1,2,4]三唑并[1,5-a]吡啶-7-羧基酰胺对应物相比，它们具有抑制人腺苷的潜力2a（hA2a）受体及其对人腺苷1（hA1）受体的选择性。基于对异构三唑并吡啶对的H键供体/受体能力的分析，可以得出结论，游离氨基官能团的H键供体强度是hA2a抑制活性和hA1选择性的主要决定因素。

  DOI：

  10.1016/j.bmcl.2004.03.104

文献信息

• Substituted triazolopyridine compounds
  申请人：——

  公开号：US20030207911A1

  公开（公告）日：2003-11-06

  A compound of formula 1 wherein R 1 is —NR′R″, wherein R′ and R″ are independently selected from the group consisting of lower alkyl, —(CH 2 ) n —C(O)NR a R b , —(CH 2 ) n -heteroaryl, —(CH 2 ) n -aryl, —(CH 2 ) n —CN, —(CH 2 ) n —O-lower alkyl or —(CH 2 ) n -cycloalkyl, or R′ and R″ form together with the N-atom a five or six-membered non- aromatic ring, containing no or one additional heteroatom selected from the group consiting of O and S, and said ring being unsubstituted or substituted by one or two substituents, selected from the group consisting of lower alkyl, —C(O)NR a R b and —(CH 2 ) n —O-lower alkyl, and R a R b are independently from each other hydrogen or lower alkyl; R 2 is aryl or heteroaryl, unsubstituted or substituted by lower alkyl or halogen; and n is 0, 1, 2 or 3; or a pharmaceutically acceptable salt thereof. Compounds of formula I are useful in the treatment of disease associated with the adenosine A2 receptor.

  式1的化合物，其中R1为—NR′R″，其中R′和R″分别选自下列基团：较低烷基，—(CH2)n—C(O)NRaRb，—(CH2)n-杂环芳基，—(CH2)n-芳基，—(CH2)n—CN，—(CH2)n—O-较低烷基或—(CH2)n-环烷基，或者R′和R″与N原子一起形成一个不含或含有O和S中选择的一个额外杂原子的五元或六元非芳香环，该环未取代或取代一个或两个取代基，所选自较低烷基，—C(O)NRaRb和—(CH2)n—O-较低烷基的基团，且RaRb各自独立为氢或较低烷基；R2为芳基或杂环芳基，未取代或取代为较低烷基或卤素；n为0、1、2或3；或其药学上可接受的盐。式I的化合物在治疗与腺苷A2受体相关的疾病中很有用。
• METHODS AND COMPOSITIONS FOR INHIBITING OR REDUCING HAIR LOSS
  申请人：The Trustees of the University of Pennsylvania

  公开号：EP3175856A1

  公开（公告）日：2017-06-07

  A non-therapeutic method of treating baldness in the scalp of a subject, the method comprising administering a prostaglandin D2 receptor (DP receptor) antagonist to the subject. The antagonist may be a prostaglandin D2 receptor 2 (DP2 receptor) antagonist.

  一种治疗受试者头皮秃发的非治疗方法，该方法包括向受试者施用前列腺素 D2 受体（DP 受体）拮抗剂。拮抗剂可以是前列腺素D2受体2（DP2受体）拮抗剂。
• Methods and compositions for inhibiting or reducing hair loss, acne, rosacea, prostate cancer, and BPH
  申请人：THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：US10849841B2

  公开（公告）日：2020-12-01

  This invention provides methods of treating androgenetic alopecia (AGA), acne, rosacea, prostate cancer, and benign prostatic hypertrophy (BPH), comprising the step of contacting a subject with a compound or composition capable of decreasing prostaglandin D2 (PGD2) level or activity, a downstream signaling or receptor pathway thereof, or prostaglandin D2 synthase level or activity; methods of stimulating hair growth, comprising the step of contacting a subject with a compound or composition capable of increasing or decreasing the activity or level of a target gene of the present invention, or with a protein product of the target gene or an analogue or mimetic thereof; and methods of testing for AGA and evaluating therapeutic methods thereof, comprising measuring PGD2 levels.

  本发明提供了治疗雄激素性脱发(AGA)、痤疮、酒渣鼻、前列腺癌和良性前列腺肥大(BPH)的方法，包括使受试者与能降低前列腺素D2(PGD2)水平或活性、其下游信号传导或受体通路或前列腺素D2合成酶水平或活性的化合物或组合物接触的步骤；刺激毛发生长的方法，包括使受试者接触能提高或降低本发明靶基因活性或水平的化合物或组合物，或接触靶基因的蛋白产物或其类似物或模拟物；以及检测 AGA 和评估其治疗方法的方法，包括测量 PGD2 水平。
• 8-AMINO- 1,2,4]TRIAZOLO 1,5-A]PYRIDINE-6-CARBOXYLIC ACID AMIDE
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1435952A1

  公开（公告）日：2004-07-14
• METHODS AND COMPOSITIONS FOR INHIBITING OR REDUCING HAIR LOSS, ACNE, ROSACEA, PROSTATE CANCER, AND BPH
  申请人：Cotsarelis George

  公开号：US20110021599A1

  公开（公告）日：2011-01-27

  This invention provides methods of treating androgenetic alopecia (AGA), acne, rosacea, prostate cancer, and benign prostatic hypertrophy (BPH), comprising the step of contacting a subject with a compound or composition capable of decreasing prostaglandin D2 (PGD2) level or activity, a downstream signaling or receptor pathway thereof, or prostaglandin D2 synthase level or activity; methods of stimulating hair growth, comprising the step of contacting a subject with a compound or composition capable of increasing or decreasing the activity or level of a target gene of the present invention, or with a protein product of the target gene or an analogue or mimetic thereof; and methods of testing for AGA and evaluating therapeutic methods thereof, comprising measuring PGD2 levels.