2-allyl-1-(3-pyridyl)-1,3-propanediol | 125246-31-3

• 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: 2-allyl-1-(3-pyridyl)-1,3-propanediol
• 英文别名: 2-allyl-1-(pyridin-3-yl)-1,3-propanediol；2-prop-2-enyl-1-pyridin-3-ylpropane-1,3-diol
• CAS: 125246-31-3
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: HRDGURJLQOBSPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 2-allyl-1-(3-pyridyl)-1,3-propanediol 在 对甲苯磺酸 作用下， 反应 18.0h， 生成 (4S,5R)-5-allyl-2,2-dimethyl-4-(3-pyridyl)-1,3-dioxane 、 trans-5-allyl-2,2-dimethyl-4-(3-pyridyl)-1,3-dioxane
  参考文献：
  名称：

  Dual-Acting Thromboxane Receptor Antagonist/Synthase Inhibitors: Synthesis and Biological Properties of [2-Substituted-4-(3-pyridyl)-1,3-dioxan-5-yl]alkenoic Acids

  摘要：

  The design, synthesis, and pharmacology of a new class of compounds possessing both thromboxane receptor antagonist and thromboxane synthase inhibitory properties are described. Replacement of the phenol group of the known thromboxane antagonist series 4(Z)-6-[(4RS,5SR)-4-(2-hydroxyphenyl)-1,3-dioxan-5-yl]hex-4-enoic acid by a 3-pyridyl group led to a series of compounds, 5, which were potent thromboxane synthase inhibitors and weak thromboxane antagonists. Further modifications at the dioxane C2 position led to compounds, 7, which were potent dual-acting agents. In the case of compound 7w, the dual activity was shown to reside almost exclusively in the (-)-enantiomer, 7x. Following oral dosing to rats and dogs, 7x (3 mg/kg) displayed significant dual activity over a period of at least 8 h.

  DOI：

  10.1021/jm00004a014
• 作为产物：
  描述：

  methyl 2-nicotinyl-4-pentenoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以102.3 g的产率得到2-allyl-1-(3-pyridyl)-1,3-propanediol
  参考文献：
  名称：

  Dual-Acting Thromboxane Receptor Antagonist/Synthase Inhibitors: Synthesis and Biological Properties of [2-Substituted-4-(3-pyridyl)-1,3-dioxan-5-yl]alkenoic Acids

  摘要：

  The design, synthesis, and pharmacology of a new class of compounds possessing both thromboxane receptor antagonist and thromboxane synthase inhibitory properties are described. Replacement of the phenol group of the known thromboxane antagonist series 4(Z)-6-[(4RS,5SR)-4-(2-hydroxyphenyl)-1,3-dioxan-5-yl]hex-4-enoic acid by a 3-pyridyl group led to a series of compounds, 5, which were potent thromboxane synthase inhibitors and weak thromboxane antagonists. Further modifications at the dioxane C2 position led to compounds, 7, which were potent dual-acting agents. In the case of compound 7w, the dual activity was shown to reside almost exclusively in the (-)-enantiomer, 7x. Following oral dosing to rats and dogs, 7x (3 mg/kg) displayed significant dual activity over a period of at least 8 h.

  DOI：

  10.1021/jm00004a014

文献信息

• Pyridine derivatives
  申请人：Imperial Chemical Industries PLC

  公开号：US05053415A1

  公开（公告）日：1991-10-01

  The invention concerns novel, pharmaceutically useful 1,3-dioxane alkenoic acid derivatives of the formula I containing a pyridyl moiety at position 4 of the dioxane ring and in which the groups at positions 2, 4 and 5 have cis-relative stereochemistry, X is hydrogen, alkoxy or hydroxy, Y is vinylene, n is 1 or 2, A.sup.1 is alkylene, the substituents R.sup.1 and R.sup.2 at position 2 of the dioxane ring have a variety of values defined hereinafter, and R.sup.4 is hydroxy, a physiologically acceptable alcohol residue or alkanesulphonamido, and the pharmaceutically acceptable salts thereof. The invention also includes processes for the manufacture and use of the acid derivatives as well as pharmaceutical compositions for therapeutic use in one or more of a variety of diseases such as ischaemic heart disease, cerebrovascular disease, asthmatic disease and/or inflammatory disease.

  本发明涉及一类新型的、具有药物活性的1,3-二氧杂环戊烷烯酸衍生物，其通式为I，其中二氧杂环戊烷环的第4位含有吡啶基团，且第2、4和5位的基团具有顺式相对立体化学结构，X是氢、烷氧基或羟基，Y是乙烯基，n是1或2，A.sup.1是亚烷基，二氧杂环戊烷环第2位的取代基R.sup.1和R.sup.2具有多种后续定义的值，而R.sup.4是羟基、生理上可接受的醇残基或烷磺酰胺基，以及它们的药物可接受盐。本发明还包括制造和使用这些酸衍生物的方法，以及用于治疗多种疾病如缺血性心脏病、脑血管病、哮喘病和/或炎症性疾病的药物组合物。
• 4-pyridyl substituted-1,3-dioxane compounds
  申请人：Imperial Chemical Industries PLC

  公开号：US05166213A1

  公开（公告）日：1992-11-24

  The invention concerns novel, pharmaceutically useful 1,3-dioxane alkenoic acid derivatives of the formula I containing a pyridyl moiety at position 4 of the dioxane ring and in which the groups at positions 2, 4 and 5 have cis-relative stereochemistry, X is hydrogen, alkoxy or hydroxy, Y is vinylene, n is 1 or 2, A.sup.1 is alkylene, R.sup.1 is a variety of substituents defined hereinafter, and R.sup.2 is hydroxy, a physiologically acceptable alcohol residue or alkanesulphonamido, and the pharmaceutically acceptable salts thereof. The invention also includes processes for the manufacture and use of the acid derivatives as well as pharmaceutical compositions for therapeutic use in one or more of a variety of diseases such as ischaemic heart disease, cerebrovascular disease, asthmatic disease and/or inflammatory disease.

  这项发明涉及一种新颖的、具有药用价值的1,3-二氧杂环戊烯酸衍生物，其化学式为I，其中在二氧杂环丁烷环的4位含有吡啶基团，且在2、4和5位的基团具有顺式立体化学构型，X为氢、烷氧基或羟基，Y为乙烯基，n为1或2，A.sup.1为烷基，R.sup.1为下文定义的各种取代基，R.sup.2为羟基、生理学上可接受的醇残基或烷磺酰胺基，以及其药用盐。该发明还包括制造和使用这些酸衍生物的方法，以及用于治疗各种疾病的药物组合物，如缺血性心脏病、脑血管疾病、哮喘疾病和/或炎症性疾病。
• 4-pyridyl-1,3-dioxane derivatives
  申请人：Zeneca Limited

  公开号：US05401849A1

  公开（公告）日：1995-03-28

  The invention concerns pharmaceutically useful 1,3-dioxane alkenoic acid derivatives of formula VII and formula XI containing a pyridyl moiety at position 4 of the dioxane ring and in which the groups at positions 2, 4 and 5 have cis-relative stereochemistry, wherein X is hydrogen, alkoxy or hydroxy, Y is vinylene, n is 1 or 2, A.sup.1 is alkylene, R.sup.1 is a variety of substituents defined hereinafter, Ra and Rb are independently methyl or ethyl, R.sup.2 is hydroxy, a physiologically acceptable alcohol residue or alkanesulphonamido, and the pharmaceutically acceptable salts thereof.

  本发明涉及具有药用价值的1,3-二氧杂环己烯烯酸衍生物，其分子式为VII和XI式，其中在二氧杂环己烯环的4位上含有吡啶基团，且2、4和5位上的基团具有顺式构型，其中X为氢、烷氧基或羟基，Y为乙烯基，n为1或2，A.sup.1为烷基，R.sup.1为下文所定义的各种取代基，Ra和Rb独立地为甲基或乙基，R.sup.2为羟基、生理上可接受的醇残基或烷基磺酰胺基，以及其药学上可接受的盐。
• Pyridyl substituted alkenoic acid derivatives
  申请人：Imperial Chemical Industries, Plc

  公开号：US05248780A1

  公开（公告）日：1993-09-28

  The invention concerns novel, pharmaceutically useful 1,3-dioxane alkenoic acid derivatives of the formula I containing a pyridyl moiety at position 4 of the dioxane ring and in which the groups at positions 2, 4 and 5 have cis-relative stereochemistry, X is hydrogen, alkoxy or hydroxy, Y is vinylene, n is 1 or 2, A.sup.1 is alkylene, R.sup.1 is a variety of substituents defined hereinafter, and R.sup.2 is hydroxy, a physiologically acceptable alcohol residue or alkanesulphonamido, and the pharmaceutically acceptable salts thereof. The invention also includes processes for the manufacture and use of the acid derivatives as well as pharmaceutical compositions for therapeutic use in one or more of a variety of diseases such as ischaemic heart disease, cerebrovascular disease, asthmatic disease and/or inflammatory disease.

  本发明涉及新型、具有药用价值的1,3-二噁烷烯酸衍生物，其式子为I，其中在二噁烷环的4位含有吡啶基团，2、4和5位上的基团具有顺式立体化学，X为氢、烷氧基或羟基，Y为乙烯基，n为1或2，A.sup.1为烷基，R.sup.1为下文中定义的各种取代基，R.sup.2为羟基、生理上可接受的醇残基或烷基磺酰胺基，以及其药学上可接受的盐。本发明还包括制造和使用该酸衍生物的方法，以及用于治疗缺血性心脏病、脑血管病、哮喘病和/或炎症性疾病等多种疾病的药物组合物。
• US5053415A
  申请人：——

  公开号：US5053415A

  公开（公告）日：1991-10-01