2-benzylsulfanyl-4-chlorothiazole-5-carbaldehyde | 918131-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-benzylsulfanyl-4-chlorothiazole-5-carbaldehyde
• 英文别名: 2-benzylsulfanyl-4-chloro-1,3-thiazole-5-carbaldehyde
• CAS: 918131-29-0
• 化学式: C₁₁H₈ClNOS₂
• 分子量: 269.776
• InChiKey: YCUZSRCNCRKZDV-UHFFFAOYSA-N

物化性质

• 沸点：
  434.7±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzylsulfanyl-4-chlorothiazole-5-carbaldehyde 、 3-benzylthiazolin-2,4-dione 在 sodium acetate 、 溶剂黄146 作用下， 反应 12.0h， 以49.59%的产率得到3-benzyl-5-(2-benzylsulfanyl-4-chloro-thiazol-5-yl-methylene)-2,4-thiazolidinedione
  参考文献：
  名称：

  Bozdag-Duendar, Oya; Ceylan-Uenluesoy, Meltem; Verspohl, Eugen J., Arzneimittel-Forschung/Drug Research, 2006, vol. 56, # 9, p. 621 - 625

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二氯噻唑-5-甲醛 、 苄硫醇 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 21.0h， 以81.84%的产率得到2-benzylsulfanyl-4-chlorothiazole-5-carbaldehyde
  参考文献：
  名称：

  Bozdag-Duendar, Oya; Ceylan-Uenluesoy, Meltem; Verspohl, Eugen J., Arzneimittel-Forschung/Drug Research, 2006, vol. 56, # 9, p. 621 - 625

  摘要：

  DOI：

文献信息

• Aldose Reductase Inhibitory Potential of Several Thiazolyl-thiazolidine- 2,4-Diones
  作者：Net Das-Evcimen、Mutlu Sarıkaya、A. Selen Gurkan-Alp、Oya Bozdag-Dundar

  DOI：10.2174/1570180811310050008

  日期：2013.4.1

  Hyperglycemia has been shown to be the major risk factor responsible for the systemic complications that are the cause of morbidity and mortality in patients with diabetes. The elevated glucose concentration in blood, activates several pathways such as polyol pathway, PKC pathway, hexosamine pathway and plays an important role not only in cataract but also in the pathogenesis of diabetic complications such as neuropathy, nephropathy and retinopathy. The activation of polyol pathway through aldose reductase enzyme leads to accumulate sorbitol in tissues during diabetic stage. Accumulation of sorbitol causes diabetic complications such as cataract, kidney disease. Inhibition of aldose reductase enzyme activity would be an effective treatment of diabetic complications. In the present study, 21 thiazolyl-2,4- thiazolidinediones (TZDs) (compounds 1-21) were tested for their probable inhibitory ability on kidney aldose reductase enzyme. The enzyme activity was determined spectrophotometrically by monitoring NADPH oxidation which accompanies the reduction of D -L-glyceraldehyde which is used as substrate. The inhibition study was performed merely by using 10-4 M concentration of each drug and IC50 values of compounds 1-6, 16-21 were studied. 10-4, 10-5 and 10-6M concentrations were performed for calculating IC50 values. Compound 1 (5-((2, 4-dichlorothiazol-5-yl) methylene) thiazolidine-2, 4-dione) is showed the greatest inhibition capacity with the rate 91.11%. TZD-derivatives which have the compound numbers 2, 5, 16 and 20 are followed the compound 1 with the inhibition capacities of 77.50%, 81.31%, 77.36% and 78.97%, respectively. All the remaining TZD-derivatives are showed inhibitory activity between the rates 4.00 - 76.58 %.

  高血糖已被证明是导致全身并发症的主要危险因素，而全身并发症是糖尿病患者发病和死亡的原因。血液中葡萄糖浓度升高会激活多种途径，如多元醇途径、PKC 途径、己胺途径，不仅在白内障中起重要作用，而且在神经病变、肾病变和视网膜病变等糖尿病并发症的发病机制中也起重要作用。在糖尿病阶段，通过醛糖还原酶激活多元醇途径会导致山梨醇在组织中积累。山梨醇的积累会导致白内障、肾病等糖尿病并发症。抑制醛糖还原酶的活性可有效治疗糖尿病并发症。本研究测试了 21 种噻唑基-2,4-噻唑烷二酮类化合物（TZDs）（化合物 1-21）对肾脏醛糖还原酶的可能抑制能力。通过监测 NADPH 氧化（伴随着作为底物的 D -L -甘油醛的还原），以分光光度法测定酶的活性。抑制研究仅使用 10-4 M 浓度的每种药物，并研究了 1-6、16-21 号化合物的 IC50 值。计算 IC50 值的浓度分别为 10-4、10-5 和 10-6M。化合物 1（5-（（2，4-二氯噻唑-5-基）亚甲基）噻唑烷-2，4-二酮）的抑制能力最强，抑制率为 91.11%。化合物编号为 2、5、16 和 20 的 TZD 衍生物的抑制能力紧随化合物 1 之后，分别为 77.50%、81.31%、77.36%和 78.97%。其余所有 TZD 衍生物的抑制活性均在 4.00 - 76.58 % 之间。
• Bozdag-Duendar, Oya; Ceylan-Uenluesoy, Meltem; Verspohl, Eugen J., Arzneimittel-Forschung/Drug Research, 2006, vol. 56, # 9, p. 621 - 625
  作者：Bozdag-Duendar, Oya、Ceylan-Uenluesoy, Meltem、Verspohl, Eugen J.、Ertan, Rahmiye

  DOI：——

  日期：——