methyl 2-nicotinyl-4-pentenoate | 130204-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-nicotinyl-4-pentenoate
• 英文别名: methyl 2-nicotinoyl-4-pentenoate；methyl 2-(pyridine-3-carbonyl)pent-4-enoate
• CAS: 130204-98-7
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: JTGNBPWLANLNEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-nicotinyl-4-pentenoate 在 sodium azide 、 碘苯二乙酸 、 三苯基膦 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 12.5h， 生成 3'-(Methoxycarbonyl)-5'-(phenylseleno)-1',4',5',6'-tetrahydro-3,2'-bipyridine
  参考文献：
  名称：

  Synthesis of nitrogen-containing heterocycles from the azido-selenenylation products of unsaturated carbonyl compounds

  摘要：

  Terminal alkenes containing a remote carbonyl group reacted with iodobenzene diacetate, diphenyl diselenide, and sodium azide to afford the products of azido-phenylselenenylation of the double bond. Owing to its radical nature, this reaction proceeded with complete anti-Markovnikov regioselectivity. Under the influence of triphenylphosphine in benzene the azido group reacted with the carbonyl function to afford the corresponding ring-closure reaction products containing a carbon nitrogen double bond. Thus, starting from beta,gamma- or gamma,delta-unsaturated esters, the corresponding cyclic imino ethers were obtained. These could not be isolated but were directly transformed into beta-(phenylseleno) gamma-lactams or gamma-(phenylseleno) delta-lactams. The phenylseleno derivatives of tetrahydropyridine were formed starting both from gamma,delta-unsaturated ketones and from alpha-allyl beta-keto esters. In the latter case, the cyclization reaction is chemoselective and involves the ketonic carbonyl. The oxidation of these compounds with hydrogen peroxide directly produced the corresponding pyridines via selenoxide elimination followed by dehydrogenation. This simple reaction sequence represents a very useful general method to build up a 2-substituted pyridine ring. Several alkyl-, aryl-, and heteroarylpyridines, bipyridines, and a terpyridine have been prepared.

  DOI：

  10.1021/jo00074a042
• 作为产物：
  描述：

  烟酰乙酸甲酯 、 3-溴丙烯 在 sodium methylate 作用下， 生成 methyl 2-nicotinyl-4-pentenoate
  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

• 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。
• 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.

  本发明涉及一种新型的、具有药用价值的1,3-二氧杂环烯酸衍生物，其化学式为I，其中在二氧杂环烷环的4位上含有吡啶基团，且在2、4和5位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，2位的取代基R.sup.1和R.sup.2具有以下定义的多种取值，R.sup.4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、脑血管疾病、哮喘病和/或炎症性疾病等多种疾病的药物组合物。
• US5166213A
  申请人：——

  公开号：US5166213A

  公开（公告）日：1992-11-24