4-oxo-4-(3-thiazolidyl)-butanoic acid | 110301-45-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-oxo-4-(3-thiazolidyl)-butanoic acid
• 英文别名: 4-Oxo-4-(1,3-thiazolidin-3-yl)butanoic acid
• CAS: 110301-45-6
• 化学式: C₇H₁₁NO₃S
• 分子量: 189.235
• InChiKey: CBCIVTQLSZLGOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-oxo-4-(3-thiazolidyl)-butanoic acid 、 紫朱牛舌草(ALKANNATINCTORIA)根提取物 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.25h， 以34.7%的产率得到1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-oxo-4-(thiazolidin-3-yl)butanoate
  参考文献：
  名称：

  Novel naphthalene-enoates: Design and anticancer activity through regulation cell autophagy

  摘要：

  Eleven dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl) naphthalene derivatives as anticancer agents through regulating cell autophagy were designed and synthesized. The anticancer activity results indicated that most compounds manifested obvious un-toxic effect on GES-1 and L-02 with IC50 from 0.58 to 1.41 mM. Among them, (S, Z)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(3,4-dihydroisoquinolin- 2(1 H)-yl)-4-oxobut-2-enoate (compound 4i) could induce cancer cells apoptosis. Further experiments showed that autophagy played an important role in the pro-apoptotic effect of this compound. Preliminary mechanism indicated that this compound could inhibit phosphoinositide 3-kinase/protein kinase B and the mammalian target of rapamycin (PI3K/AKT/mTOR) pathway by mediating apoptosis in an autophagy-dependent manner.

  DOI：

  10.1016/j.biopha.2019.108747
• 作为产物：
  描述：

  丁二酸酐 、 噻唑烷盐酸盐 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 生成 4-oxo-4-(3-thiazolidyl)-butanoic acid
  参考文献：
  名称：

  Thiazolidine derivatives, process for their preparation and pharmaceutical compositions

  摘要：

  式I中的化合物，其中A代表：- 饱和或不饱和的非环状残基；- 饱和的环状或杂环残基；- 饱和或不饱和的双环残基；R代表OH、C₁-C₄烷氧基团或直链或杂环氨基残基；R₁代表氢、烷基团或芳香或杂芳香残基。化合物I具有宝贵的治疗特性。

  公开号：

  EP0222371A3

文献信息

• Thiazolidine derivatives, process for their preparation and
  申请人：Chiesi Farmaceutici S.p.A.

  公开号：US04775676A1

  公开（公告）日：1988-10-04

  Compounds of formula I ##STR1## wherein A represents: a saturated or unsaturated acyclic residue; a saturated cyclic or heterocyclic residue; a saturated or unsaturated bicyclic residue; and R represents OH, a C.sub.1 -C.sub.4 alkoxy group or a straight or heterocycle aminoresidue; R.sub.1 represents hydrogen, an alkyl group or an aromatic or heteroaromatic residue. Compounds I are endowed with valuable therapeutic characteristics.

  式I的化合物，其中A代表：饱和或不饱和的无环残基；饱和的环状或杂环残基；饱和或不饱和的双环残基；R代表OH，C.sub.1 -C.sub.4烷氧基团或直链或杂环氨基残基；R.sub.1代表氢，烷基团或芳香或杂芳香残基。化合物I具有宝贵的治疗特性。
• Novel naphthalene-enoates: Design and anticancer activity through regulation cell autophagy
  作者：Meng Di Yang、Xiao Bao Shen、Yang Sheng Hu、Yan Yan Chen、Xin Hua Liu

  DOI：10.1016/j.biopha.2019.108747

  日期：2019.5

  Eleven dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl) naphthalene derivatives as anticancer agents through regulating cell autophagy were designed and synthesized. The anticancer activity results indicated that most compounds manifested obvious un-toxic effect on GES-1 and L-02 with IC50 from 0.58 to 1.41 mM. Among them, (S, Z)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(3,4-dihydroisoquinolin- 2(1 H)-yl)-4-oxobut-2-enoate (compound 4i) could induce cancer cells apoptosis. Further experiments showed that autophagy played an important role in the pro-apoptotic effect of this compound. Preliminary mechanism indicated that this compound could inhibit phosphoinositide 3-kinase/protein kinase B and the mammalian target of rapamycin (PI3K/AKT/mTOR) pathway by mediating apoptosis in an autophagy-dependent manner.
• Thiazolidine derivatives, process for their preparation and pharmaceutical compositions
  申请人：CHIESI FARMACEUTICI S.p.A.

  公开号：EP0222371A3

  公开（公告）日：1989-11-29

  Compounds of formula I wherein A represents: - a saturated or unsaturated acyclic residue; - a saturated cyclic or heterocylic residue; - a saturated or unsaturated bicyclic residue and R represents OH, a C₁-C₄ alkoxy group or a straight or heterocycle aminoresidue; R₁ represents hydrogen, an alkyl group or an aromatic or heteroaromatic residue.Compounds I are endowed with valuable therapeutic characteristics.

  式I中的化合物，其中A代表：- 饱和或不饱和的非环状残基；- 饱和的环状或杂环残基；- 饱和或不饱和的双环残基；R代表OH、C₁-C₄烷氧基团或直链或杂环氨基残基；R₁代表氢、烷基团或芳香或杂芳香残基。化合物I具有宝贵的治疗特性。