9-(5-formylthien-2-yl)nonanoic acid methyl ester | 78845-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 9-(5-formylthien-2-yl)nonanoic acid methyl ester
• 英文别名: Methyl 9-(5-formylthiophen-2-yl)nonanoate
• CAS: 78845-75-7
• 化学式: C₁₅H₂₂O₃S
• 分子量: 282.404
• InChiKey: SYRVPWFRUBEXGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(5-formylthien-2-yl)nonanoic acid methyl ester 在 哌啶 、 sodium hydroxide 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 4.5h， 生成 9-[5-((E)-2-Carboxy-vinyl)-thiophen-2-yl]-nonanoic acid
  参考文献：
  名称：

  Inverse agonists at the polyamine-sensitive modulatory site of the NMDA receptor: 50-fold increase in potency by insertion of an aromatic ring into an alkanediamine chain

  摘要：

  Polyamines like spermine and spermidine increase the opening frequency of the NMDA receptor associated ion channel and, as a consequence, specific binding of non-saturating concentrations of the channel radioligand [H-3]MK-801. Compounds exhibiting the contrary effect have been described as polyamine inverse agonists, with 1,12-dodecanediamine (N-12-N) being one of the most specific ones (IC50 16.5 mu M). Here we describe the synthesis of a series of long-chain alkanediamines, with a thiophene nucleus inserted at various positions, and report the discovery of 5-(4-aminobutyl)-2-thiopheneoctanamine (N-4-T-8-N), which inhibited specific binding of [H-3]MK-801 by 50 % at 0.33 mu M. In the presence of 100 mu M of spermine, 4.0 mu M N-4-T-8-N was necessary to achieve the same degree of inhibition. N-4-T-8-N is the most potent polyamine inverse agonist presently known and should be a useful tool to elucidate the physiological significance of the polyamine regulatory site of the NMDA receptor complex. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80070-1
• 作为产物：
  描述：

  9-thiophen-2-yl-nonanoic acid 在 氯化亚砜 、 三氯氧磷 作用下， 生成 9-(5-formylthien-2-yl)nonanoic acid methyl ester
  参考文献：
  名称：

  Inverse agonists at the polyamine-sensitive modulatory site of the NMDA receptor: 50-fold increase in potency by insertion of an aromatic ring into an alkanediamine chain

  摘要：

  Polyamines like spermine and spermidine increase the opening frequency of the NMDA receptor associated ion channel and, as a consequence, specific binding of non-saturating concentrations of the channel radioligand [H-3]MK-801. Compounds exhibiting the contrary effect have been described as polyamine inverse agonists, with 1,12-dodecanediamine (N-12-N) being one of the most specific ones (IC50 16.5 mu M). Here we describe the synthesis of a series of long-chain alkanediamines, with a thiophene nucleus inserted at various positions, and report the discovery of 5-(4-aminobutyl)-2-thiopheneoctanamine (N-4-T-8-N), which inhibited specific binding of [H-3]MK-801 by 50 % at 0.33 mu M. In the presence of 100 mu M of spermine, 4.0 mu M N-4-T-8-N was necessary to achieve the same degree of inhibition. N-4-T-8-N is the most potent polyamine inverse agonist presently known and should be a useful tool to elucidate the physiological significance of the polyamine regulatory site of the NMDA receptor complex. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80070-1

文献信息

• Alkenyl-substituted thienylalkanecarboxylic acids and derivatives thereof
  申请人：A. Nattermann & Cie. GmbH

  公开号：US04309407A1

  公开（公告）日：1982-01-05

  The invention provides novel .omega.-(5-alkenylthien-2-yl)alkanecarboxylic acids and their functional derivatives having the formula ##STR1## wherein n is an integer from 1 to 9, inclusive; R.sup.1 is H and R.sup.2 is --OH, or R.sup.1 and R.sup.2 together with the wavy lines represent a keto group; and R.sup.3 is H, C.sub.1 -C.sub.6 straight or branched-chain saturated hydrocarbon, or a pharmaceutically acceptable alkali cation. The 3-oxoalkenyl-substituted compounds of formula (I) are prepared by a Wittig-Horner reaction using a 2-oxoheptylphosphonic acid dialkyl ester and an aldehyde of the formula ##STR2## as starting materials, while the 3-hydroxyalkenyl-substituted compounds are obtained by reduction of the corresponding 3-oxoalkenyl compounds. The esters of formula (I) can also be readily converted to the corresponding acids and salts of formula (I). The compounds of the invention have valuable anti-inflammatory, antipyretic and anti-arteriosclerotic properties, yet have low toxicity and do not irritate the gastric mucosa.

  本发明提供了具有以下结构的新型ω-(5-烯基噻吩-2-基)烷基羧酸及其功能衍生物：其中n是1到9之间的整数；R^1是H，R^2是—OH，或者R^1和R^2与波浪线一起表示酮基；R^3是H，C1-C6直链或支链饱和碳氢化合物，或者是药用可接受的碱金属阳离子。公式(I)的3-氧代烯基取代化合物通过使用2-氧代庚基膦酸二烷基酯和具有以下结构的醛作为起始原料，经Wittig-Horner反应制备，而3-羟基烯基取代化合物通过还原相应的3-氧代烯基化合物获得。公式(I)的酯也可以方便地转化为相应的酸和盐。本发明的化合物具有有价值的抗炎、退热和抗动脉硬化特性，且毒性低，不刺激胃粘膜。
• Alkenyl-thienyl-alkancarbonsäuren und ihre Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
  申请人：A. Nattermann & Cie. GmbH

  公开号：EP0029247B1

  公开（公告）日：1983-04-13
• US4309407A
  申请人：——

  公开号：US4309407A

  公开（公告）日：1982-01-05
• Inverse agonists at the polyamine-sensitive modulatory site of the NMDA receptor: 50-fold increase in potency by insertion of an aromatic ring into an alkanediamine chain
  作者：Michael L. Berger、Clemens Schödl、Christian R. Noe

  DOI：10.1016/s0223-5234(99)80070-1

  日期：1998.1

  Polyamines like spermine and spermidine increase the opening frequency of the NMDA receptor associated ion channel and, as a consequence, specific binding of non-saturating concentrations of the channel radioligand [H-3]MK-801. Compounds exhibiting the contrary effect have been described as polyamine inverse agonists, with 1,12-dodecanediamine (N-12-N) being one of the most specific ones (IC50 16.5 mu M). Here we describe the synthesis of a series of long-chain alkanediamines, with a thiophene nucleus inserted at various positions, and report the discovery of 5-(4-aminobutyl)-2-thiopheneoctanamine (N-4-T-8-N), which inhibited specific binding of [H-3]MK-801 by 50 % at 0.33 mu M. In the presence of 100 mu M of spermine, 4.0 mu M N-4-T-8-N was necessary to achieve the same degree of inhibition. N-4-T-8-N is the most potent polyamine inverse agonist presently known and should be a useful tool to elucidate the physiological significance of the polyamine regulatory site of the NMDA receptor complex. (C) Elsevier, Paris.