3-(4-acetyl-5-methyl-1H-pyrrol-3-yl)propanoic acid | 38664-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-acetyl-5-methyl-1H-pyrrol-3-yl)propanoic acid
• 英文别名: 3-acetyl-4-(2-carboxyethyl)-2-methylpyrrole；4-acetyl-3-(2-carboxyethyl)-5-methylpyrrole；3-(4-acetyl-5-methyl-pyrrol-3-yl)-propionic acid；3-(4-Acetyl-5-methyl-pyrrol-3-yl)-propionsaeure；1H-Pyrrole-3-propanoic acid, 4-acetyl-5-methyl-
• CAS: 38664-17-4
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: PNZIZPJYPBTHTM-UHFFFAOYSA-N

物化性质

• 沸点：
  397.5±42.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  70.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-acetyl-5-methyl-1H-pyrrol-3-yl)propanoic acid 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以30%的产率得到3-(4-Acetyl-2-chloro-5-methyl-1H-pyrrol-3-yl)-propionic acid
  参考文献：
  名称：

  Assessment of the active-site requirements of 5-aminolevulinic acid dehydratase: evaluation of substrate and product analogs as competitive inhibitors

  摘要：

  DOI：

  10.1021/jo00044a041
• 作为产物：
  描述：

  3-(4-acetyl-3-hydroxy-5-methyl-2,4-dihydropyrrol-3-yl)propanoic acid 以95%的产率得到
  参考文献：
  名称：

  Butler Anthony R., George Sharon D., J. Chem. Soc. Perkin Trans. 2, (1994) N 2, S 315-318

  摘要：

  DOI：

文献信息

• Competing Knorr and Fischer–Fink pathways to pyrroles in neutral aqueous solution
  作者：Vanampally Chandrashaker、Masahiko Taniguchi、Marcin Ptaszek、Jonathan S. Lindsey

  DOI：10.1016/j.tet.2012.05.080

  日期：2012.8

  solution at pH 7 for 24 h afforded the Knorr pyrrole and Fischer–Fink pyrrole in yields of 48% and 7%, respectively. The reaction in hot aqueous acid (pH 4.6, reflux, 30 min) afforded the Knorr pyrrole in diminished yield (22%) relative to that of the Fischer–Fink pyrrole (11%). The Knorr pyrrole (4-ethyl-2,3-dimethylpyrrole) is evanescent whereas the Fischer–Fink pyrrole (2,3,4-trimethyl-5-propanoylpyrrole)

  拟议的四吡咯大环前生化学模型基于3-烷基取代的2,4-二酮和α-氨基酮的缩合形成吡咯，可用于随后的自缩合，从而形成卟啉原。非环状反应物的缩合可通过竞争性克诺尔（所希望的）和费希尔-芬克（不想要的）途径来进行。这里，克诺尔和Fischer-芬克途径是使用那些在所提出的益生元的路由，其中所得的吡咯从随后的缩合受阻，和（2）通过对粗反应混合物的定量组的内部标准（1）的类似物定量1萃取到CS 2中后的1 H NMR光谱。1-氨基-2-丁酮和3-甲基-2,4-戊二酮在60°C的水溶液中在pH 7的条件下反应24小时，得到的克诺尔吡咯和费歇尔-芬克吡咯的收率分别为48％和7％ ， 分别。在热酸水溶液中（pH 4.6，回流，30分钟）进行反应，相对于费-芬克吡咯（11％），克诺尔吡咯的收率降低了（22％）。克诺尔吡咯（4-乙基-2,3-二甲基吡咯）是渐逝性的，而菲舍尔-芬克吡咯（2,3,4-三甲基-5-
• Reaction of some diketones with 5-aminolevulinic acid in acid solution
  作者：Anthony R Butler、Sharon D George

  DOI：10.1016/s0040-4020(01)87976-x

  日期：1993.8

  Some 2,4-diketones react with 5-aminolevulinic acid in acid solution to form pyrroles. There are two modes of cyclisation, one leading to the Knorr and the other to the Fischer-Fink product. By a consideration of the products obtained from pentane-, hexane-, 3-methylpentane-, 3-isopropylpentane-, 3,3-dimethylpentane-, 1,1,1-trifluoropentane- 1,1,1,5,5,5-hexafluoro- pentane-2,4-dione and ethyl acetoacetate

  一些2,4-二酮与5-氨基乙酰丙酸在酸性溶液中反应形成吡咯。环化有两种模式，一种通向克诺尔，另一种通向费歇尔·芬克产品。考虑到从戊烷-，己烷-，3-甲基戊烷-，3-异丙基戊烷-，3,3-二甲基戊烷-，1,1,1-三氟戊烷-1,1,1,5,5,5获得的产物-六氟戊烷-2,4-二酮和乙酰乙酸乙酯已对Knorr和Fischer-Fink产品的形成作了一些概括。还研究了5-甲基-5-氨基乙酰丙酸与戊烷和3-甲基戊烷-2,4-二酮的反应。简要讨论了这些研究与5-氨基乙酰丙酸的环状二聚化的相关性。
• <i>Michael</i>Reactions of α-Unsubstituted Trisubstituted 1<i>H</i>-Pyrroles
  作者：Rainer Lüönd、Reinhard Neier

  DOI：10.1002/hlca.19910740111

  日期：1991.1.30

  To obtain stable derivatives of α-unsubstituted pyrroles, the reaction of the test pyrrole 9 with a series of chalcones 14a–h were studied. Michael adducts 16b–h could be isolated. In order to synthesize coloured derivatives, the reaction of different pyrroles 9, 21, 23, and 25 with diphenylpropynone 19 was investigated. In these cases, too, Michael-addition products were formed. The intense absorption

  为了获得稳定的α-未取代吡咯衍生物，研究了吡咯9与一系列查耳酮14a – h的反应。迈克尔加合物16b – h可以隔离。为了合成有色衍生物，不同吡咯的反应9，21，23，和25与diphenylpropynone 19进行了研究。在这些情况下，也形成了迈克尔加成产物。400 nm附近的强吸收带使这些衍生物的鉴定变得容易。
• Discovery of Pyrrole−Indoline-2-ones as Aurora Kinase Inhibitors with a Different Inhibition Profile
  作者：Chao-Cheng Chiang、Yu-Hsiang Lin、Shu Fu Lin、Chun-Liang Lai、Chiawei Liu、Win-Yin Wei、Sheng-chuan Yang、Ru-Wen Wang、Li-Wei Teng、Shih-Hsien Chuang、Jia-Ming Chang、Ta-Tung Yuan、Ying-Shuen Lee、Paonien Chen、Wei-Kuang Chi、Ju-Ying Yang、Hung-Jyun Huang、Chu-Bin Liao、Jiann-Jyh Huang

  DOI：10.1021/jm1001869

  日期：2010.8.26

  A series of pyrrole-indolin-2-ones were synthesized, and their inhibition profile for Aurora kinases was studied. The potent compound 33 with phenylsulfonamido at the C-5 position and a carboxyethyl group at the C-3' position selectively inhibited Aurora A over Aurora B with IC(50) values of 12 and 156 nM, respectively. Replacement of the carboxyl group with an amino group led to compound 47, which retained the activity for Aurora B and lost activity for Aurora A (IC(50) = 2.19 mu M). Computation modeling was used to address the different inhibition profiles of 33 and 47. Compounds 47 and 36 (the ethyl ester analogue of 33) inhibited the proliferation of HCT-116 and HT-29 cells and suppressed levels of the phosphorylated substrates of Aurora A and Aurora B in the Western blots.
• Mauzerall; Granick, Journal of Biological Chemistry, 1956, vol. 219, p. 435,443
  作者：Mauzerall、Granick

  DOI：——

  日期：——