methyl 3-methoxy-4-(pyridin-4-yl)benzoate | 859140-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 3-methoxy-4-(pyridin-4-yl)benzoate
• 英文别名: Methyl 3-methoxy-4-pyridin-4-ylbenzoate
• CAS: 859140-23-1
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: RAZNVBMVXSFLDH-UHFFFAOYSA-N

物化性质

• 沸点：
  353.4±32.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-methoxy-4-(pyridin-4-yl)benzoate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 47.55h， 生成 1-[(6-chloro-2-naphthyl)sulfonyl]-4-[3-methoxy-4-(4-pyridyl)benzoyl]piperazine
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006
• 作为产物：
  描述：

  4-溴-3-甲氧基苯甲酸甲酯 、 4-二乙基吡啶硼烷 在 四(三苯基膦)钯 氢氧化钾 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 以92%的产率得到methyl 3-methoxy-4-(pyridin-4-yl)benzoate
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006

文献信息

• Design, Synthesis, and Evaluation of Reversible and Irreversible Monoacylglycerol Lipase Positron Emission Tomography (PET) Tracers Using a “Tail Switching” Strategy on a Piperazinyl Azetidine Skeleton
  作者：Zhen Chen、Wakana Mori、Xiaoyun Deng、Ran Cheng、Daisuke Ogasawara、Genwei Zhang、Michael A. Schafroth、Kenneth Dahl、Hualong Fu、Akiko Hatori、Tuo Shao、Yiding Zhang、Tomoteru Yamasaki、Xiaofei Zhang、Jian Rong、Qingzhen Yu、Kuan Hu、Masayuki Fujinaga、Lin Xie、Katsushi Kumata、Yuancheng Gou、Jingjin Chen、Shuyin Gu、Liang Bao、Lu Wang、Thomas Lee Collier、Neil Vasdev、Yihan Shao、Jun-An Ma、Benjamin F. Cravatt、Christopher Fowler、Lee Josephson、Ming-Rong Zhang、Steven H. Liang

  DOI：10.1021/acs.jmedchem.8b01778

  日期：2019.4.11

  and [18F]37 ([18F]MAGL-4-11) also demonstrated excellent in vivo binding specificity toward MAGL in peripheral organs. This work may pave the way for the development of MAGL-targeted positron emission tomography tracers with tunability in reversible and irreversible binding mechanisms.

  单酰基甘油脂酶（MAGL）是丝氨酸水解酶，可降解内源性大麻素系统（eCB）中的2-花生四烯酸甘油酯（2-AG）。MAGL的选择性抑制已成为治疗多种病理状况（包括慢性疼痛，炎症，癌症和神经变性）的潜在治疗方法。本文中，我们通过在哌嗪基氮杂环丁烷支架上的“尾部转换”公开了可逆和不可逆的MAGL抑制剂的新型阵列。我们开发了一种不可逆结合的先导MAGL抑制剂8和可逆结合的化合物17和37，它们适用于用11C或18F进行放射性标记。[11C] 8（[11C] MAGL-2-11）在大脑中对MAGL表现出高脑摄取和极好的结合特异性。可逆放射性配体[11C] 17（[11C] PAD）和[18F] 37（[18F] MAGL-4-11）也表现出对外周器官MAGL的出色体内结合特异性。这项工作可能为以可逆和不可逆结合机制的可调性为目标的以MAGL为目标的正电子发射断层显像示踪剂的开发铺平道路。
• Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites
  作者：Satoshi Komoriya、Noriyasu Haginoya、Shozo Kobayashi、Tsutomu Nagata、Akiyoshi Mochizuki、Masanori Suzuki、Toshiharu Yoshino、Haruhiko Horino、Takayasu Nagahara、Makoto Suzuki、Yumiko Isobe、Taketoshi Furugoori

  DOI：10.1016/j.bmc.2005.04.006

  日期：2005.6

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.