(1,2,4-triazol-1-ylmethyl)-(thien-2-yl)-ketone | 108664-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1,2,4-triazol-1-ylmethyl)-(thien-2-yl)-ketone
• 英文别名: 1-thiophen-2-yl-2-(1,2,4-triazol-1-yl)ethanone
• CAS: 108664-57-9
• 化学式: C₈H₇N₃OS
• 分子量: 193.229
• InChiKey: FDNVDIIPASNKBT-UHFFFAOYSA-N

物化性质

• 沸点：
  423.8±51.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1,2,4-triazol-1-ylmethyl)-(thien-2-yl)-ketone 在 甲酸 、 [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以93%的产率得到(S)-1-(thiophen-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-ol
  参考文献：
  名称：

  Catalytic asymmetric synthesis of β-triazolyl amino alcohols by asymmetric transfer hydrogenation of α-triazolyl amino alkanones

  摘要：

  The synthesis of optically active beta-triazolyl amino alcohols was carried out via ruthenium catalyzed asymmetric transfer hydrogenation of alpha-triazolyl amino alkanones. This reaction proceeds under mild reaction conditions with up to 99% yield and 99.9% enantiomeric excess (ee). This protocol was applied to the synthesis of an enantiopure antitubercular agent and its arylated product with retention in enantiomeric purity. The absolute configuration at the stereogenic center of the chiral product as found to be (S). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.05.012
• 作为产物：
  描述：

  2-乙酰基噻吩 在 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 0.75h， 生成 (1,2,4-triazol-1-ylmethyl)-(thien-2-yl)-ketone
  参考文献：
  名称：

  Synthesis and antifungal activity of a series of novel 1,2-disubstituted propenones

  摘要：

  To find an antifungal agent other than those of the imidazole and triazole series, a new class of 1,2-disubstituted propenones I and II was prepared and tested for antifungal activity. Comparison of the structure-activity relationships showed that the conjugated structure of carbonyl and exomethylene groups in I and II plays an important role in potent antifungal activity. However, it is noteworthy that compounds 53, 54, and 56, which have a hydroxymethyl or methoxymethyl group instead of an exo-methylene group in I, also showed potent activity. Although many compounds exhibited strong antifungal activity in vitro, none showed activity in vivo of oral efficacy against subacute systemic candidiasis in mice.

  DOI：

  10.1021/jm00391a037

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2004011410A1

  公开（公告）日：2004-02-05

  Compounds of formula (I):wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  式(I)的化合物：其中变量基团如定义内；用于抑制11βHSD1。
• Synthesis and cell imaging applications of fluorescent mono/di/tri-heterocyclyl-2,6-dicyanoanilines
  作者：Mahesh M. Pisal、Ritesh A. Annadate、Meghana C. Athalye、Deepak Kumar、Subhash P. Chavan、Dhiman Sarkar、Hanumant B. Borate

  DOI：10.1016/j.bmcl.2016.12.074

  日期：2017.2

  contact but not the nucleus while the compound 12 showed affinity to apoptotic cells resulting in blue fluorescence. The cell imaging results with compound 12 were similar to Annexin V-FITC, a known reagent containing recombinant Annexin V conjugated to green-fluorescent FITC dye, used for detection of apoptotic cells. These compounds were found to be non-cytotoxic and have potential application as cell

  描述了从杂环醛和1,2-二杂环取代的乙酮开始的3,4,5-三杂环基-2,6-二氰基苯胺的合成。还已经合成了具有一个或两个杂环取代基的2，6-二氰基苯胺。发现这些分子中的一些具有对细胞成像应用有用的选择性细胞染色特性。化合物1克，10F和11被发现在接触细胞的细胞质染色但不同时化合物核12产生蓝色荧光凋亡细胞显示出亲和力。化合物12的细胞成像结果与膜联蛋白V-FITC相似，膜联蛋白V-FITC是一种已知试剂，包含与绿色荧光FITC染料偶联的重组膜联蛋白V，用于检测凋亡细胞。发现这些化合物是无细胞毒性的，并且具有作为细胞显像剂的潜在应用。
• Ketones
  申请人：Barton John Peter

  公开号：US20050272036A1

  公开（公告）日：2005-12-08

  Compounds of formula (I): wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  描述了式(I)的化合物：其中变量基团如定义的那样；用于抑制11βHSD1。
• Mullen, Goerge B.; Bennett, Grace A.; Swift, Patricia A., Liebigs Annalen der Chemie, 1989, p. 389 - 392
  作者：Mullen, Goerge B.、Bennett, Grace A.、Swift, Patricia A.、Kuipers, William J.、Georgiev, Vassil St.

  DOI：——

  日期：——
• MULLEN, GEORGE B.;BENNETT, GRACE A.;SWIFT, PATRICIA A.;KUIPERS, WILLIAM J+, LIEBIGS ANN. CHEM.,(1989) N, C. 389-392
  作者：MULLEN, GEORGE B.、BENNETT, GRACE A.、SWIFT, PATRICIA A.、KUIPERS, WILLIAM J+

  DOI：——

  日期：——