(E)-3-thiazol-2-ylpropenal | 185947-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-3-thiazol-2-ylpropenal
• 英文别名: (2E)-3-(1,3-thiazol-2-yl)prop-2-enal；(e)-3-Thiazol-2-yl-propenal；(E)-3-(1,3-thiazol-2-yl)prop-2-enal
• CAS: 185947-62-0
• 化学式: C₆H₅NOS
• 分子量: 139.178
• InChiKey: HZDGKHNJPKBPHP-OWOJBTEDSA-N

物化性质

• 沸点：
  272.6±42.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-thiazol-2-ylpropenal 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 25.5h， 生成 (2S,3S,4E)-2-amino-3-hydroxy-5-thiazol-2-yl-pent-4-enoic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of δ-heteroaryl substituted β-hydroxy-γ,δ-unsaturated α-amino acids

  摘要：

  Enantiomerically pure 6-heteroaryl substituted beta-hydroxy-gamma, delta-unsaturated alpha-amino acids were stereoselectively synthesized starting from (2R)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkoffs reagent) and suitable beta-heteroaryl-alpha, beta-unsaturated aldehydes. The stereocontrolled addition gave a mixture of two diastereoisomers whose configurations were assigned on the basis of spectroscopic data and the accepted model for aldol condensation of the Schollkoffs reagent. Upon controlled hydrolysis the adducts were transformed into the corresponding methyl esters of 6-heteroaryl substituted beta-hydroxy-gamma,delta-unsaturated alpha-amino acids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.023
• 作为产物：
  描述：

  2-醛基噻唑 、 甲酰甲撑基三苯基磷 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-3-thiazol-2-ylpropenal
  参考文献：
  名称：

  1,9-二杂芳基nona-1,3,6,8-四烯基5-ones作为新型抗前列腺癌药物的设计，合成和生物学评估

  摘要：

  为了寻求更有效的化学疗法来治疗去势抵抗性前列腺癌并受到姜黄素类似物的启发，二十五个（1 E，3 E，6 E，8 E）-1,9-diarylnona-1,3,6,8通过Wittig反应，然后进行Horner-Wadsworth-Emmons反应，已成功合成了带有两个相同末端杂芳族环的-tetraen-5-ones。其中的二十三种是新化合物。WST-1细胞增殖测定法用于评估其对雄激素敏感性和雄激素敏感性人类前列腺癌细胞系的抗增殖作用。与姜黄素相比，二十五个合成化合物中有十八个具有显着改善的效能。最佳化合物78在抑制前列腺癌细胞增殖方面，β-内啡肽的活性比姜黄素高14到23倍。从我们的数据可以得出结论，1,9-二芳基壬娜-1,3,6,8-四烯基5-one可以作为开发抗前列腺癌药物和吡啶-4-基的新的潜在支架。和喹啉-4-基充当最佳杂芳环，以增强该支架的效能。两种最有效的化合物68和75通过激活细胞凋亡和将细胞周期阻滞在G

  DOI：

  10.1016/j.bmc.2016.08.006

文献信息

• 2-Acyl-3-carboxyl-tetrahydroisoquinoline Derivatives: Mixed-Type PTP1B Inhibitors without PPARγ Activation
  作者：Ko Morishita、Yoshimichi Shoji、Masaki Fukui、Yuma Ito、Tatsuya Kitao、Shin-ichiro Ozawa、Shuichi Hirono、Hiroaki Shirahase

  DOI：10.1248/cpb.c18-00571

  日期：2018.12.1

  oquinoline derivatives were synthesized and biologically evaluated. Among them, (S)-2-(E)-3-furan-2-ylacryloyl}-7-[(2E,4E)-5-(2,4,6-trifluorophenyl)penta-2,4-dienyloxy]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (compound 17u) was identified as a potent protein tyrosine phosphatase 1B (PTP1B) inhibitor without peroxisome proliferator-activated receptor (PPAR) γ activation: PTP1B inhibition IC50=0

  合成了一系列新颖的2-酰基-3-羧基-四氢异喹啉衍生物，并对其进行了生物学评估。其中，（S）-2-（（E）-3-呋喃-2-基丙烯酰基）-7-[（2E，4E）-5-（2,4,6-三氟苯基）戊-2,4-二烯氧基] -1,2,3,4-四氢异喹啉-3-羧酸（化合物17u）被确定为有效的蛋白酪氨酸磷酸酶1B（PTP1B）抑制剂，无过氧化物酶体增殖物激活受体（PPAR）γ激活：PTP1B抑制作用IC50 = 0.19 µM，PPARγEC50> 10 µM。化合物17u对PTP1B表现出混合型抑制作用，这种抑制模式通过计算配体对接到PTP1B的催化位点和变构位点而得以合理化。化合物17u在大鼠中也表现出较高的口服吸收，剂量为10 mg / kg（每os（口服），Cmax = 4.67 µM），在以db的最终给药后24小时进行的口服葡萄糖耐量试验中，在30 mg / kg / d（po）下连续4周显着
• Quinoline derivatives as antibacterials
  申请人：——

  公开号：US20040053928A1

  公开（公告）日：2004-03-18

  Aminopiperidine derivatives and pharmaceutically acceptable derivatives thereof useful in methods of treatment of bacterial infections in mammals, particularly in man.

  氨氧哌啶衍生物及其药用可接受的衍生物，用于治疗哺乳动物，特别是人类的细菌感染。
• Flindersia Alkaloids, Derivatives and Analogs: Compositions and Methods for Producing the Same
  申请人：May Jeremy A.

  公开号：US20130190511A1

  公开（公告）日：2013-07-25

  The present invention provides methods for chemically synthesizing naturally-occurring alkaloids, for example, Flindersia alkaloids, and their analogs and derivatives. Generally, the precursor borrerine is synthesized from tryptamine in the presence of an alkylating agent, an acylating agent and a reducing agent and dimerized in the presence of an acid, for example, tetrafluoroacetic acid, hydrochloric acid or acetic acid to yield the products. Analog and derivative compounds are produced by derivatizing one or more of the tryptamine, alkylating agent or acylating agent. Also provided are the synthetic alkaloids and derivatives and analogs thereof produced by the synthetic methods.

  本发明提供了一种用于化学合成天然生物碱的方法，例如，Flindersiaalkaloids及其类似物和衍生物。通常，前体borrerine在存在烷基化剂、酰化剂和还原剂的情况下从色胺合成，并在酸的存在下（例如四氟乙酸、盐酸或乙酸）发生二聚反应，产生产物。通过对色胺、烷基化剂或酰化剂中的一个或多个进行衍生化，可以生产类似物和衍生物化合物。此外，本发明还提供了通过合成方法制备的合成生物碱及其衍生物和类似物。
• Structure-activity relationship studies of 1,7-diheteroarylhepta-1,4,6-trien-3-ones with two different terminal rings in prostate epithelial cell models
  作者：Rubing Wang、Xiaojie Zhang、Chengsheng Chen、Guanglin Chen、Cristian Sarabia、Qiang Zhang、Shilong Zheng、Guangdi Wang、Qiao-Hong Chen

  DOI：10.1016/j.ejmech.2017.03.067

  日期：2017.6

  To systematically investigate the structure-activity relationships of 1,7-diarylhepta-1,4,6-trien-3-ones in three human prostate cancer cell models and one human prostate non-neoplastic epithelial cell model, thirty five 1,7-diarylhepta-1,4,6-trien-3-ones with different terminal heteroaromatic rings have been designed for evaluation of their anti-proliferative potency in vitro. These target compounds have been successfully synthesized through two sequential Horner-Wadsworth-Emmons reactions starting from the appropriate aldehydes and tetraethyl (2-oxopropane-1,3-diyl)bis(phosphonate). Their anti-proliferative potency against PC-3, DU-145 and LNCaP human prostate cancer cell lines can be significantly enhanced by the manipulation of the terminal heteroaromatic rings, further demonstrating the utility of 1,7-diarylhepta-1,4,6-trien-3-one as a potential scaffold for the development of anti prostate cancer agents. The optimal analog 40 is 82-, 67-, and 39-fold more potent than curcumin toward the three prostate cancer cell lines, respectively. The experimental data also reveal that the trienones with two different terminal aromatic rings possess greater potency toward three prostate cancer cell lines, but also have greater capability of suppressing the proliferation of PWR-1E benign human prostate epithelial cells, as compared to the corresponding counterparts with two identical terminal rings and curcumin. The terminal aromatic rings also affect the cell apoptosis perturbation. (C) 2017 Elsevier Masson SAS. All rights reserved.
• QUINOLINE DERIVATIVES AS ANTIBACTERIALS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1320529A1

  公开（公告）日：2003-06-25