5-(4-(cyclohexylmethoxy)benzyl)thiazolidine-2,4-dione | 74773-24-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-(cyclohexylmethoxy)benzyl)thiazolidine-2,4-dione
• 英文别名: 5-[(4-cyclohexylmethoxyphenyl)methyl]thiazolidine-2,4-dione；5-[[4-(cyclohexylmethoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 74773-24-3
• 化学式: C₁₇H₂₁NO₃S
• 分子量: 319.425
• InChiKey: CUTOEBXNDMBJRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  环己甲醇 在 palladium on activated charcoal copper(I) oxide 、 盐酸 、 氢气 、 sodium acetate 、 sodium hydride 、 sodium nitrite 作用下， 以 甲醇 、 乙二醇甲醚 、 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 17.5h， 生成 5-(4-(cyclohexylmethoxy)benzyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Studies on antidiabetic agents. II. Synthesis of 5-(4-(1-methylcyclohexylmethoxy)-benzyl)thiazolidine-2,4-dione (ADD-3878) and its derivatives.

  摘要：

  合成了100多种5-取代的噻唑烷-2,4-二酮类化合物，并通过遗传性肥胖和糖尿病小鼠（KK黄色小鼠）评估了它们的降血糖和降血脂活性。结构-活性关系研究表明，5-(4-羟基苄基)部分对于显著活性是必要的。在这些化合物中，5-(4-环己基甲氧基)苄基噻唑烷-2,4-二酮（47）、5-[4-(1-甲基环己基甲氧基)苄基]-噻唑烷-2,4-二酮（49，ADD-3878）和5-{4-[2-(3-吡啶基)乙氧基]苄基}噻唑烷-2,4-二酮（59）在活性和毒性方面表现出最佳特性。

  DOI：

  10.1248/cpb.30.3580

文献信息

• Studies on antidiabetic agents. II. Synthesis of 5-(4-(1-methylcyclohexylmethoxy)-benzyl)thiazolidine-2,4-dione (ADD-3878) and its derivatives.
  作者：TAKASHI SOHDA、KATSUTOSHI MIZUNO、EIKO IMAMIYA、YASUO SUGIYAMA、TAKESHI FUJITA、YUTAKA KAWAMATSU

  DOI：10.1248/cpb.30.3580

  日期：——

  More than 100 5-substituted thiazolidine-2, 4-diones were prepared and their hypoglycemic and hypolipidemic activities were evaluated with genetically obese and diabetic mice, yellow KK. The structure-activity relationship study showed that the 5-(4-oxybenzyl) moiety is essential for substantial activity. Among these compounds, 5-(4-cyclohexylmethoxy) benzylthiazolidine-2, 4-dione (47), 5-[4-(1-methylcyclohexylmethoxy) benzyl]-thiazolidine-2, 4-dione (49, ADD-3878) and 5-4-[2-(3-pyridyl) ethoxy] benzyl} thiazolidine-2, 4-dione (59) exhibited the most favorable properties in terms of activity and toxicity.

  合成了100多种5-取代的噻唑烷-2,4-二酮类化合物，并通过遗传性肥胖和糖尿病小鼠（KK黄色小鼠）评估了它们的降血糖和降血脂活性。结构-活性关系研究表明，5-(4-羟基苄基)部分对于显著活性是必要的。在这些化合物中，5-(4-环己基甲氧基)苄基噻唑烷-2,4-二酮（47）、5-[4-(1-甲基环己基甲氧基)苄基]-噻唑烷-2,4-二酮（49，ADD-3878）和5-4-[2-(3-吡啶基)乙氧基]苄基}噻唑烷-2,4-二酮（59）在活性和毒性方面表现出最佳特性。
• NOVEL THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF
  申请人：Cho Hoon

  公开号：US20110269954A1

  公开（公告）日：2011-11-03

  The present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and the uses thereof. More specifically, the present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and a pharmaceutical composition comprising the same. The novel thiazolidinedione derivatives of formula (I) according to the present invention can be effectively used for the prevention or treatment of cardiovascular disease, gastrointestinal disease and renal disease by inhibiting the activity of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) that decomposes prostaglandins as well as useful for the prevention of hair loss and the stimulation of hair growth, and osteogenic stimulation and wound healing.

  本发明涉及由以下式（I）表示的新型噻唑烷二酮衍生物及其用途。更具体地说，本发明涉及由以下式（I）表示的新型噻唑烷二酮衍生物以及包含其的药物组合物。根据本发明的式（I）的新型噻唑烷二酮衍生物可以通过抑制分解前列腺素的15-羟基前列腺素脱氢酶（15-PGDH）的活性，有效用于预防或治疗心血管疾病、胃肠道疾病和肾脏疾病，同时也用于预防脱发和促进头发生长，以及促进骨生成和伤口愈合。
• 미세조류 파괴용 조성물
  申请人：Industry-Academic Cooperation Foundation, Chosun University 조선대학교산학협력단(220050171903) BRN ▼408-82-13419

  公开号：KR20160126772A

  公开（公告）日：2016-11-02

  본 개시는 미세조류 파괴용 조성물에 관한 것으로, 상기 미세조류 파괴용 조성물은 해양 미세조류 배양장, 녹조 또는 적조가 발생된 지역 또는 녹조나 적조 발생 예상 지역에 처리되어 미세조류의 생장 및 증식을 억제함으로써, 녹조 및 적조 피해를 예방할 수 있는 효과가 있다.

  本发明涉及微藻破坏性配方，所述微藻破坏性配方被处理在海洋微藻培养场、褐藻或红藻爆发区域或者预计褐藻或红藻爆发的区域，通过抑制微藻的生长和繁殖，可以预防褐藻和红藻的危害。
• Thiazolidinedione derivative and use thereof
  申请人：Cho Hoon

  公开号：US08637558B2

  公开（公告）日：2014-01-28

  The present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and the uses thereof. More specifically, the present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and a pharmaceutical composition comprising the same. The novel thiazolidinedione derivatives of formula (I) according to the present invention can be effectively used for the prevention or treatment of cardiovascular disease, gastrointestinal disease and renal disease by inhibiting the activity of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) that decomposes prostaglandins as well as useful for the prevention of hair loss and the stimulation of hair growth, and osteogenic stimulation and wound healing.

  本发明涉及以下式(I)所表示的新型噻唑烷二酮衍生物及其用途。更具体地说，本发明涉及以下式(I)所表示的新型噻唑烷二酮衍生物及其制备的药物组合物。根据本发明的新型噻唑烷二酮衍生物可以有效用于抑制降解前列腺素的15-羟基前列腺素脱氢酶（15-PGDH）的活性，从而预防或治疗心血管疾病、胃肠道疾病和肾脏疾病，并且有助于预防脱发和促进头发生长，以及促进骨生成和伤口愈合。
• Thiazolidinediones as hypoglycemic and anti-atherosclerosis agents
  申请人：PFIZER INC.

  公开号：EP0319189A1

  公开（公告）日：1989-06-07

  The present invention relates to compounds of the formula wherein the broken line is an optional bond, and the pharmaceutically acceptable cationic salts thereof, having utility as hypoglycemic and anti-atherosclerosis agents, and pharmaceutical compositions containing them.

  本发明涉及如下式的化合物 其中断线为任选键的化合物及其药学上可接受的阳离子盐，它们具有降血糖和抗动脉粥样硬化的作用，以及含有它们的药物组合物。