5-methoxy-2-phenylpyrazolo[1,5-a]pyridine | 403495-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methoxy-2-phenylpyrazolo[1,5-a]pyridine
• CAS: 403495-92-1
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: CVNBPXCBVVENFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-phenylpyrazolo[1,5-a]pyridine 在 tin 、 sodium tetrahydroborate 、 盐酸甲胺 、 potassium acetate 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 313.83h， 生成 N-[2-(5-methoxy-2-phenylpyrazolo[1,5-a]pyridin-3-yl)ethyl]butanamide
  参考文献：
  名称：

  Bicyclic melatonin receptor agonists containing a ring-junction nitrogen: Synthesis, biological evaluation, and molecular modeling of the putative bioactive conformation

  摘要：

  Employing 1,3-dipolar cycloaddition for the synthesis of the 7a-azaindole nucleus, analogues of melatonin have been synthesized and tested against human and amphibian melatonin receptors. Introducing a phenyl substituent ill position 2 of the heterocyclic moiety significantly increased binding affinity to both the MT1 and MT2 receptors. Shifting the methoxy group from position 5 to 2 of the 7a-azaindole ring led to a substantial reduction of MT1 binding when MT2 recognition was maintained. We theoretically investigated the hypothesis whether the 2-methoxy function of the azamelatonin analogue 27 is able to mimic the 5-methoxy group of the neurohormone by directing its 2-methoxy function toward the methoxy binding site. DFT calculations and experimental binding differences of analogue compounds indicate that the energy gained by forming the methoxy-specific hydrogen-bond interaction should exceed the energy required for adopting ail alternative conformation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.042
• 作为产物：
  描述：

  methyl 5-methoxy-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate 在 水 、 potassium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 5-methoxy-2-phenylpyrazolo[1,5-a]pyridine
  参考文献：
  名称：

  EP2669285

  摘要：

  公开号：

文献信息

• Novel pyrazolo[1,5- a ]pyridines as orally active EP 1 receptor antagonists: Synthesis, structure-activity relationship studies, and biological evaluation
  作者：Kentaro Umei、Yosuke Nishigaya、Atsushi Kondo、Kazuya Tatani、Nobuyuki Tanaka、Yasushi Kohno、Shigeki Seto

  DOI：10.1016/j.bmc.2017.03.003

  日期：2017.5

  Novel pyrazolo[1,5-a]pyridine derivatives were designed, synthesized and evaluated as orally active EP1 antagonists for the treatment of overactive bladder. Matched molecular pair analysis (MMPA) allowed the design of a new series of pyrazolo[1,5-a]pyridine derivatives 4-6. Structure-activity relationships (SAR) studies of 4-6 were performed, leading to identification of the nanomolar-level EP1 antagonist

  设计，合成和评价新型吡唑并[1,5-a]吡啶衍生物作为口服活性EP1拮抗剂，用于治疗膀胱过度活动症。匹配的分子对分析（MMPA）允许设计一系列新的吡唑并[1,5-a]吡啶衍生物4-6。进行了4-6的结构-活性关系（SAR）研究，鉴定了纳摩尔水平的EP1拮抗剂4c，在17-苯基trinor前列腺素E2诱导的膀胱收缩模型中，通过十二指肠内（id）给药显示出良好的药理作用在大鼠中。
• Pyrazolopyridine compound and pharmaceutical use thereof
  申请人：——

  公开号：US20040110763A1

  公开（公告）日：2004-06-10

  A pyrazolopyridine compound of formula (I) wherein: R 1 is hydrogen, lower alkyl optionally substituted by susbtituent(s), or cyclo(lower)alkyl which may be interrupted by an oxygen or nitrogen atom and optionally substituted by substituent(s); R 2 is hydrogen, halogen or lower alkoxy; R 3 is a substituent; and n is an integer from 1 to 4, provided R 3 may be different from each other when n is 2, 3 or 4, or a salt thereof. The pyrazolopyridine compound (I) and salt thereof of the present invention are adnosine antagonists and are useful for the prevention and/or treatment of depression, dementia (e.g. Alzheimer's disease, cerebrovascular dementia, dementia accompanying Parkinson's disease, etc.) Parkinson's disease, anxiety, pain, cerebrovascular disease (e.g. stroke, etc.), heart failure and the like. 1

  化合物(I)为吡唑吡啶化合物，其化学式为：其中，R1为氢、低碳基（可选择性地被取代）或环（低）烷基，其可由氧或氮原子中断，且可选择性地被取代；R2为氢、卤素或低烷氧基；R3为取代基；n为1至4的整数，但当n为2、3或4时，R3可能彼此不同，或其盐。本发明的吡唑吡啶化合物(I)及其盐为腺苷受体拮抗剂，可用于预防和/或治疗抑郁症、痴呆症（例如阿尔茨海默病、脑血管痴呆、帕金森病伴随痴呆等）、帕金森病、焦虑症、疼痛、脑血管疾病（例如中风等）、心力衰竭等疾病。
• PYRAZOLOPYRIDINE DERIVATIVE OR PHARMACOLOGICALLY ACCEPTABLE SALT THEREOF
  申请人：Seto Shigeki

  公开号：US20130331378A1

  公开（公告）日：2013-12-12

  A pyrazolopyridine derivative represented by the following formula (I) or a pharmacologically acceptable salt thereof exhibits a strong EP 1 receptor antagonistic effect. Thus, the derivative or the pharmacologically acceptable salt is useful as a therapeutic agent for lower urinary tract symptoms (LUTS), particularly, overactive bladder syndrome (OABs), or a prophylactic agent therefor and furthermore, is also useful in the treatment, prevention, or suppression of various pathological conditions in which the EP 1 receptor is involved, such as inflammatory disease, pain disease, osteoporosis, and cancer. [A is a benzene ring or the like, Y 1 is C 1-6 alkylene, R 1 is —C(═O)—OZ 1 or the like, Z 1 is H or the like, R 2 is a branched C 3-6 alkyl group or the like, R 3 is H or the like, R 4 is a hydrogen atom or the like, and R 5 is a hydrogen atom or the like].

  以下式(I)所表示的吡唑吡啶衍生物或其药学上可接受的盐，表现出强烈的EP1受体拮抗作用。因此，该衍生物或药学上可接受的盐可用作下尿路症状（LUTS），特别是过度活跃膀胱综合症（OABs）的治疗剂或预防剂，此外，它还可用于治疗、预防或抑制EP1受体参与的各种病理情况，如炎症性疾病、疼痛疾病、骨质疏松症和癌症。其中，A为苯环或类似物，Y1为C1-6烷基，R1为-C（═O）-OZ1或类似物，Z1为H或类似物，R2为支链C3-6烷基或类似物，R3为H或类似物，R4为氢原子或类似物，R5为氢原子或类似物。
• Discovery of novel pyrazolo[1,5-a]pyridine-based EP1 receptor antagonists by scaffold hopping: Design, synthesis, and structure-activity relationships
  作者：Yosuke Nishigaya、Kentaro Umei、Yoshifumi Saito、Hiroyuki Watanabe、Tatsuhiro Kondo、Atsushi Kondo、Naohiro Kawamura、Kazuya Tatani、Yasushi Kohno、Nobuyuki Tanaka、Shigeki Seto

  DOI：10.1016/j.bmcl.2017.07.055

  日期：2017.9

  A scaffold-hopping strategy towards a new pyrazolo[1,5-a]pyridine based core using molecular hybridization of two structurally distinct EP1 antagonists, followed by structure-activity relationship guided optimization, resulted in the identification of potent EP1 antagonists exemplified by 4c, 4f, and 4j, which were shown to reduce pathological intravesical pressure in rats when administered at 1 mg/kg iv. (C) 2017 Published by Elsevier Ltd.
• EP2669285
  申请人：——

  公开号：——

  公开（公告）日：——