4-[2-(Oxan-2-yl)ethoxy]benzaldehyde | 1221413-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[2-(Oxan-2-yl)ethoxy]benzaldehyde
• 英文别名: 4-[2-(oxan-2-yl)ethoxy]benzaldehyde
• CAS: 1221413-88-2
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: AXNCBTSMWMUVEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-噻唑烷二酮 、 4-[2-(Oxan-2-yl)ethoxy]benzaldehyde 在 哌啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以88.2%的产率得到5-(4-(2-(tetrahydro-2H-pyran-2-yl)ethoxy)benzylidene)-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and SAR of thiazolidinedione derivatives as 15-PGDH inhibitors

  摘要：

  Prostaglandins have a short life in vivo because they are metabolized rapidly by oxidation to 15-ketoprostaglandins catalyzed by a cytosolic enzyme known as NAD(+)-dependent 15-hydroxyprostaglandin dehydrogenase (15-PGDH). Previously, CT-8, a thiazolidinedione analogue, was found to be a potent inhibitor of 15-PGDH. Structure-activity analysis indicated that the N-methylation of thiazolidine-2,4-dione, CT-8, abolished the inhibitory activity, whereas the introduction of an ethyl hydroxyl group at amine in CT-8 still had a good inhibitory effect. Based on the structures of the thiazolidinediones analogues and inhibitory activity, a range of benzylidene thiazolidinedione derivatives were synthesized with different substituents on the phenyl ring and their inhibitory activity was evaluated. Replacement of the cyclohexylethyl group of CT-8 with the hetero five-member ring increased the inhibitory potency. However, replacement of the cyclohexylethyl group with a hetero six-member ring decreased the inhibitory potency significantly. It was found that compound 2 (5-(4-(2-(thiophen-2yl) ethoxy) benzylidene) thiazolidine-2,4-dione) was the most potent inhibitor that was effective in the nanomolar range. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.016
• 作为产物：
  描述：

  2-(四氢-2H-吡喃-2-基)乙醇 、 对羟基苯甲醛 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 4-[2-(Oxan-2-yl)ethoxy]benzaldehyde
  参考文献：
  名称：

  Synthesis and SAR of thiazolidinedione derivatives as 15-PGDH inhibitors

  摘要：

  Prostaglandins have a short life in vivo because they are metabolized rapidly by oxidation to 15-ketoprostaglandins catalyzed by a cytosolic enzyme known as NAD(+)-dependent 15-hydroxyprostaglandin dehydrogenase (15-PGDH). Previously, CT-8, a thiazolidinedione analogue, was found to be a potent inhibitor of 15-PGDH. Structure-activity analysis indicated that the N-methylation of thiazolidine-2,4-dione, CT-8, abolished the inhibitory activity, whereas the introduction of an ethyl hydroxyl group at amine in CT-8 still had a good inhibitory effect. Based on the structures of the thiazolidinediones analogues and inhibitory activity, a range of benzylidene thiazolidinedione derivatives were synthesized with different substituents on the phenyl ring and their inhibitory activity was evaluated. Replacement of the cyclohexylethyl group of CT-8 with the hetero five-member ring increased the inhibitory potency. However, replacement of the cyclohexylethyl group with a hetero six-member ring decreased the inhibitory potency significantly. It was found that compound 2 (5-(4-(2-(thiophen-2yl) ethoxy) benzylidene) thiazolidine-2,4-dione) was the most potent inhibitor that was effective in the nanomolar range. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.016

文献信息

• [EN] BENZOTHIOPHENES<br/>[FR] BENZOTHIOPHENES
  申请人：ELI LILLY AND COMPANY

  公开号：WO1999007693A1

  公开（公告）日：1999-02-18

  (EN) This invention provides novel benzothiophene compounds of formula (I), which are useful for the treatment of the various medical conditions associated with postmenopausal syndrome, as well as estrogen dependent diseases including cancer of the breast, uterus, and cervix. The present invention further relates to pharmaceutical formulations of compounds of formula (I).(FR) Cette invention se rapporte à de nouveaux composés de benzothiophènes représentés par la formule (I), qui s'avèrent utiles au traitement de divers troubles associés au syndrome post-ménopausique, et des maladies à dépendance oestrogénique, notamment le cancer du sein, de l'utérus et du col utérin. La présente invention se rapporte en outre à des compositions pharmaceutiques contenant les composés représentés par la formule (I).
• Synthesis and SAR of thiazolidinedione derivatives as 15-PGDH inhibitors
  作者：Ying Wu、Hsin-Hsiung Tai、Hoon Cho

  DOI：10.1016/j.bmc.2010.01.016

  日期：2010.2

  Prostaglandins have a short life in vivo because they are metabolized rapidly by oxidation to 15-ketoprostaglandins catalyzed by a cytosolic enzyme known as NAD(+)-dependent 15-hydroxyprostaglandin dehydrogenase (15-PGDH). Previously, CT-8, a thiazolidinedione analogue, was found to be a potent inhibitor of 15-PGDH. Structure-activity analysis indicated that the N-methylation of thiazolidine-2,4-dione, CT-8, abolished the inhibitory activity, whereas the introduction of an ethyl hydroxyl group at amine in CT-8 still had a good inhibitory effect. Based on the structures of the thiazolidinediones analogues and inhibitory activity, a range of benzylidene thiazolidinedione derivatives were synthesized with different substituents on the phenyl ring and their inhibitory activity was evaluated. Replacement of the cyclohexylethyl group of CT-8 with the hetero five-member ring increased the inhibitory potency. However, replacement of the cyclohexylethyl group with a hetero six-member ring decreased the inhibitory potency significantly. It was found that compound 2 (5-(4-(2-(thiophen-2yl) ethoxy) benzylidene) thiazolidine-2,4-dione) was the most potent inhibitor that was effective in the nanomolar range. (C) 2010 Elsevier Ltd. All rights reserved.