4-氯-2-(1-哌啶)-5-噻唑甲醛 | 139670-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-氯-2-(1-哌啶)-5-噻唑甲醛
• 英文名称: 4-chloro-2-(piperidin-1-yl)thiazole-5-carbaldehyde
• 英文别名: 4-Chloro-2-(1-piperidino)-5-thiazolecarboxaldehyde；4-chloro-2-piperidin-1-yl-1,3-thiazole-5-carbaldehyde
• CAS: 139670-00-1
• 化学式: C₉H₁₁ClN₂OS
• mdl: MFCD03453084
• 分子量: 230.718
• InChiKey: PIHYBGQGFSRXQU-UHFFFAOYSA-N

物化性质

• 熔点：
  88 °C
• 沸点：
  368.0±45.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  4-氯-2-(1-哌啶)-5-噻唑甲醛 在 三甲基铝 、 三乙胺 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 4.0h， 生成 N-(4-chlorophenyl)-2-(piperidin-1-yl)thieno[2,3-d]thiazole-5-carboxamide
  参考文献：
  名称：

  Discovery of thienothiazolocarboxamide analogues as novel anti-tubercular agent

  摘要：

  In order to identify anti-tubercular agents with a novel scaffold, commercial libraries of small organic compounds were screened against a fluorescent strain of Mycobacterium tuberculosis H37Rv, using a dual phenotypic assay. Compounds were assessed against bacteria replicating in broth medium, as well as inside macrophages, and thienothiazolocarboxamide (TTCA) scaffold was identified as hit in both assays, with submicromolar inhibitory concentrations. Derivatives of TTCA were further synthesized and evaluated for their inhibitory effects on M.tuberculosis H37Rv. In the present study we report the structure-activity relationship of these TTCA derivatives. Compounds 28, 32 and 42 displayed good anti-tubercular activities, as well as favorable ADME and PK properties. Compound 42 exhibited excellent oral bioavailability in mice with high distribution to lungs, within 1 h. It was found to be efficacious in a dose dependent manner in a murine model of M. tuberculosis infection. Hence, compound 42 is now under evaluation as a potential lead candidate for treatment of tuberculosis.

  DOI：

  10.1016/j.bmc.2020.115797
• 作为产物：
  描述：

  哌啶 、 2,4-二氯噻唑-5-甲醛 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以83%的产率得到4-氯-2-(1-哌啶)-5-噻唑甲醛
  参考文献：
  名称：

  改进的2-取代的4-氯噻唑-5-甲醛的合成

  摘要：

  在室温下，使用碳酸钾在乙腈中，而不是在-78°C下，用丁基锂在四氢呋喃中进行去质子反应，建立了一种改进的2,4-二氯噻唑-5-甲醛（2）与仲胺反应的方法。该方法方便，并且3的产率甚至更高。化合物2也可以通过该方法与硫酚反应，得到4-氯-2-苯基硫代噻唑-5-甲醛4。

  DOI：

  10.1002/jhet.5570340509

文献信息

• Ultrasound promoted montmorillonite K-10 catalyzed synthesis, characterization, molecular modelling, SAR and hypoglycemic studies of new rhodanine bejeweled acridine analogues
  作者：Gangadhara Angajala、Valmiki Aruna、Pasupala Pavan、Pulikanti Guruprasad Reddy

  DOI：10.1016/j.molstruc.2021.130828

  日期：2021.10

  catalyst upto five cycles. In silico molecular docking studies were carried out to find out the effective binding affinity of the synthesized acridine analogues towards PPARγ protein (Id-2XKW). The results obtained showed that compounds 6c and 6g possess good binding interaction towards PPARγ with binding energy of -9.6 and -9.0 k.cal/mol which was greater than standard Acarbose (-8.9 k.cal/mol) and comparable

  在目前的工作中，一种有效的超声促进了 ( Z )-2-((4-chloro-2-(piperidin/morpholin-1-yl)thiazol-5-yl)methylene)-3,3,7,9 tetra甲基-3,4-二氢吖啶-1 (2 H ) -one 类似物6(ah)已经报道了使用 MK-10 催化剂通过 Knoevenagel 缩合。MK-10 由于其不同的性质和高表面积体积比，表现出对反应响应有利的特征，例如反应时间更短、后处理程序简单、反应过程干净，并且催化剂可重复使用多达五个循环，从而获得优异的产品收率. 进行了计算机分子对接研究，以找出合成的吖啶类似物对 PPARγ 蛋白 (Id-2XKW) 的有效结合亲和力。所得结果表明化合物6c和6g对 PPARγ 具有良好的结合相互作用，结合能为 -9.6 和 -9.0 k.cal/mol，高于标准阿卡波糖 (-8.9 k.cal/mol)，与标准吡格列酮
• 2,4-Disubstituted 4-(1,3-thiazol-5-yl)but-3-en-2-ones: synthetic approaches to and consequent chemical modification
  作者：Oleksii O. Kolomoitsev、Volodymyr M. Kotliar、Dmytro O. Tarasenko、Olexandre V. Buravov、Andrey O. Doroshenko

  DOI：10.1007/s00706-020-02612-7

  日期：2020.5

  AbstractArylideneketones are commonly considered as convenient starting materials for obtaining compounds of potential pharmaceutical interest. Heterocyclic α,β-unsaturated representatives of this series possess chemical and biological properties worth study in details. Particularly, substituted thiazole cycle, incorporated into such a system, allows obtaining of new biologically active products suitable

  摘要亚芳基酮通常被认为是用于获得具有潜在药用价值的化合物的方便的起始原料。该系列的杂环α，β-不饱和代表具有值得详细研究的化学和生物学特性。特别地，结合到这样的系统中的取代的噻唑循环允许获得适合于其随后的化学修饰的新的生物活性产物。在本交流中，我们将注意力集中在2,4-二卤素-5-甲酰基噻唑的背景上的2,4-二取代的4-（1,3-噻唑-5-基）but-3-en-2-ones上，其中一些相关合成方法以及进一步化学修饰的预期方向。 图形摘要
• 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。
• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• Athmani, Salah; Farhat, Mahmoud F.; Iddon, Brian, Journal of the Chemical Society. Perkin transactions I, 1992, # 8, p. 973 - 978
  作者：Athmani, Salah、Farhat, Mahmoud F.、Iddon, Brian

  DOI：——

  日期：——