2-phenyl-1-(1H-pyrrol-3-yl)ethanone | 96999-24-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-phenyl-1-(1H-pyrrol-3-yl)ethanone
• 英文别名: 3-(phenylacetyl)pyrrole
• CAS: 96999-24-5
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: KNFQGELQIJIILV-UHFFFAOYSA-N

物化性质

• 熔点：
  121-123 °C
• 沸点：
  360.7±17.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-phenyl-1-(1H-pyrrol-3-yl)ethanone 在 tris[2-(methoxyethoxy)ethyl]amine 、 sodium hydride 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 1.0h， 生成 (3-Phenylacetyl-pyrrol-1-yl)-acetic acid
  参考文献：
  名称：

  Substituted Pyrrol-1-ylacetic Acids That Combine Aldose Reductase Enzyme Inhibitory Activity and Ability To Prevent the Nonenzymatic Irreversible Modification of Proteins from Monosaccharides

  摘要：

  Starting from the known inhibitory activity of (3-benzoylpyrrol-1-yl)acetic acid (1) and (2-benzoylpyrrol-1-yl)acetic acid (II), a series of 3-aroyl and 2,4-bis-aroyl derivatives (54-75) were synthesized and tested for inhibition of aldose reductase, an enzyme involved in the appearance of diabetic complications. It was found that a number of the tested compounds exhibited considerable activity in the micromolar range. Important structural features for the potent compounds is the presence of substituents with relatively low Hammett sigma values and/ or moieties which increase their overall aromatic area. The most active derivative was the [2,4-bis(4-methoxybenzoyl)pyrrol-1-yl] acetic acid (75), with potency favorably compared to known ARIs such as tolrestat, epalrestat, zopolrestat, and fidarestat. Four selected derivatives were also evaluated for their ability to interfere with the oxidative modification of serum albumin in an in vitro experimental glycation model of diabetes mellitus. All of them showed considerable activity, comparable to the known inhibitor trolox. Our results, taken together, indicate that compound 75 combines favorably two biological activities directly connected to a number of pathological conditions related to the chronic diabetes mellitus.

  DOI：

  10.1021/jm0209477
• 作为产物：
  描述：

  α-(dimethylamino)-α-(pyrrol-3-yl)acetonitrile 在 sodium hydroxide 、 正丁基锂 、 二异丙胺 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 2-phenyl-1-(1H-pyrrol-3-yl)ethanone
  参考文献：
  名称：

  Synthesis of acylpyrroles via .alpha.-(dimethylamino)-.alpha.-pyrrolylacetonitriles

  摘要：

  DOI：

  10.1021/jo00261a027

文献信息

• Freidel-crafts acylation of 1-tert-butyldimethylsilylpyrrole, a very short and simple route to 3-substituted pyrroles.
  作者：Gerhard Simchen、Michal W. Majchrzak

  DOI：10.1016/s0040-4039(01)80846-7

  日期：1985.1
• Discovery of a Series of Phosphonic Acid-Containing Thiazoles and Orally Bioavailable Diamide Prodrugs That Lower Glucose in Diabetic Animals Through Inhibition of Fructose-1,6-Bisphosphatase
  作者：Qun Dang、Yan Liu、Daniel K. Cashion、Srinivas Rao Kasibhatla、Tao Jiang、Frank Taplin、Jason D. Jacintho、Haiqing Li、Zhili Sun、Yi Fan、Jay DaRe、Feng Tian、Wenyu Li、Tony Gibson、Robert Lemus、Paul D. van Poelje、Scott C. Potter、Mark D. Erion

  DOI：10.1021/jm101035x

  日期：2011.1.13

  Oral delivery of previously disclosed purine and benzimidazole fructose-1,6 bisphosphatase (FBPase) inhibitors via prodrugs failed, which was likely due to their high molecular wright (> 600) Therefore, a smaller scaffold was desired, and a series of phosphonic acid-containing thiazoles, which exhibited high potency against human liver FBPase (IC(50) of 10-30 nM) and high selectivity relative to other 5'-adenosinemonophosphate (AMP)-binding enzymes, were discovered using a structure-guided drug design approach The initial lead compound (30j) produced profound glucose lowering in rodent models of type 2 diabetes mellitus (T2DM) after parenteral administration Various phosphonate prodrugs were explored without success, until a novel phosphonic diamide prodrug approach was Implemented, which delivered compound 30j with good oral bioavailability (OBAV) (22-47%) Extensive lead optimization of both the thiazole FBPase inhibitors and their prodrugs culminated in the discovery of compound 35n (MB06322) as the first oral FBPase inhibitor advancing to human clinical trials as a potential treatment for T2DM
• N-(Triisopropylsilyl)pyrrole. A progenitor "par excellence" of 3-substituted pyrroles
  作者：Brian L. Bray、Peter H. Mathies、Reto Naef、Dennis R. Solas、Thomas T. Tidwell、Dean R. Artis、Joseph M. Muchowski

  DOI：10.1021/jo00313a019

  日期：1990.12

  A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the alpha-positions. 1-(Triisopropylsilyl)pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the beta-position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion induced desilylation of the products provides the corresponding 3-substituted pyrroles in good overall yields. Competitive trifluoroacetylation experiments demonstrate that substitution of TIPS-pyrrole at the alpha-positions is decelerated by a factor of > 10(4), vs pyrrole at the same sites, without affecting reactivity at the beta-positions. 1-(Triisopropylsilyl)-3-bromopyrrole (2) is readily converted into the 3-lithio compound 44 by bromine-lithium interchange with alkyllithium reagents. This previously unavailable, formal equivalent of 3-lithiopyrrole is itself an excellent source of a wide range of beta-substituted pyrroles, many of which would not be directly preparable from 1. TIPS-pyrrole can be 3,4-dihalogenated and these compounds undergo sequential halogen-metal interchange trapping reactions. This process is exemplified by an efficient, three-step synthesis of the antibiotic verrucarin E (63) from the dibromo compound 5.
• Synthesis of alkylpyrroles by the sodium borohydride reduction of acylpyrroles
  作者：Robert Greenhouse、Coral Ramirez、Joseph M. Muchowski

  DOI：10.1021/jo00216a030

  日期：1985.8
• Synthesis of 3-vinylpyrrole
  作者：Roberta Settambolo、Raffaello Lazzaroni、Tommaso Messeri、Michele Mazzetti、Piero Salvadori

  DOI：10.1021/jo00079a040

  日期：1993.12