6-chloro-2-phenylpyrazolo[1,5-a]pyridine | 1337984-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-chloro-2-phenylpyrazolo[1,5-a]pyridine
• CAS: 1337984-93-6
• 化学式: C₁₃H₉ClN₂
• 分子量: 228.681
• InChiKey: JMTZHMGQZOSXDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-chloro-2-phenylpyrazolo[1,5-a]pyridine 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 5.0h， 生成 methyl 6-[(6-chloro-2-phenylpyrazolo[1,5-a]pyridin-3-yl)(hydroxy)methyl]pyridine-2-carboxylate
  参考文献：
  名称：

  铃木-宫浦交叉偶联反应合成2-芳基吡唑并[1,5-a]吡啶

  摘要：

  摘要 方便地访问各种2-芳基化吡唑并[1,5-一个]吡啶吡唑并经由[1,5-一个]吡啶-2-基三氟甲磺酸酯使用被描述的Suzuki-Miyaura交叉偶联反应。合成了15种2-芳基吡唑并[1,5- a ]吡啶衍生物，产率为52-95％。 方便地访问各种2-芳基化吡唑并[1,5-一个]吡啶吡唑并经由[1,5-一个]吡啶-2-基三氟甲磺酸酯使用被描述的Suzuki-Miyaura交叉偶联反应。合成了15种2-芳基吡唑并[1,5- a ]吡啶衍生物，产率为52-95％。

  DOI：

  10.1055/s-0034-1381025
• 作为产物：
  描述：

  苯丙炔酸甲酯 在 水 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 27.0h， 生成 6-chloro-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 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.
• Synthesis of 2- and 2,3-Substituted Pyrazolo[1,5-<i>a</i>]pyridines: Scope and Mechanistic Considerations of a Domino Direct Alkynylation and Cyclization of <i>N</i>-Iminopyridinium Ylides Using Alkenyl Bromides, Alkenyl Iodides, and Alkynes
  作者：James J. Mousseau、James A. Bull、Carolyn L. Ladd、Angélique Fortier、Daniela Sustac Roman、André B. Charette

  DOI：10.1021/jo201303x

  日期：2011.10.21

  Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a]pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.
• Synthesis of 2-Arylpyrazolo[1,5-a]pyridines by Suzuki–Miyaura Cross-Coupling Reaction
  作者：Shigeki Seto、Kentaro Umei、Yosuke Nishigaya、Megumi Kamiya、Yasushi Kohno

  DOI：10.1055/s-0034-1381025

  日期：——

  2-arylated pyrazolo[1,5-a]pyridine via pyrazolo[1,5-a]pyridine-2-yl triflate using the Suzuki–Miyaura­ ­­cross-coupling reaction is described. Fifteen 2-arylpyrazolo[1,5-a]pyridine derivatives were synthesized in 52–95% yields. Convenient access to a variety of 2-arylated pyrazolo[1,5-a]pyridine via pyrazolo[1,5-a]pyridine-2-yl triflate using the Suzuki–Miyaura­ ­­cross-coupling reaction is described. Fifteen

  摘要 方便地访问各种2-芳基化吡唑并[1,5-一个]吡啶吡唑并经由[1,5-一个]吡啶-2-基三氟甲磺酸酯使用被描述的Suzuki-Miyaura交叉偶联反应。合成了15种2-芳基吡唑并[1,5- a ]吡啶衍生物，产率为52-95％。 方便地访问各种2-芳基化吡唑并[1,5-一个]吡啶吡唑并经由[1,5-一个]吡啶-2-基三氟甲磺酸酯使用被描述的Suzuki-Miyaura交叉偶联反应。合成了15种2-芳基吡唑并[1,5- a ]吡啶衍生物，产率为52-95％。