5-indol-3-yl-5-oxo-pentanoic acid | 837-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-indol-3-yl-5-oxo-pentanoic acid
• 英文别名: 4-(Indolyl-3-carbonyl)-buttersaeure；γ-(3-Indoyl)-buttersaeure；5-Oxo-5-(indolyl-3)-pentansaeure；4-(Indolyl-3)-buttersaeure；5-(1H-indol-3-yl)-5-oxopentanoic acid
• CAS: 837-84-3
• 化学式: C₁₃H₁₃NO₃
• mdl: MFCD01578312
• 分子量: 231.251
• InChiKey: ODUVLUWKHFDMEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  5-indol-3-yl-5-oxo-pentanoic acid 在 lithium aluminium tetrahydride 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.25h， 生成 1-bromo-5-(3-indolyl)pentane
  参考文献：
  名称：

  Novel bisubstrate analog inhibitors of serotonin N-acetyltransferase: the importance of being neutral

  摘要：

  [GRAPHICS]Linker modified novel bisubstrate analog inhibitors 4-7 for serotonin N-acetyltransferase (arylalkylamine N-acetyltransferase, AANAT) have been designed and synthesized. Examination of these inhibitors with AANAT in vitro suggested that: (i) linker hydrogen bonding makes only modest contributions to the affinity of bisubstrate analog inhibitors studied; (ii) greater than or equal to four methylene groups between the indole and the coenzyme A (CoASH) moieties are required for a bisubstrate analog inhibitor to achieve strong AANAT inhibition; (iii) the AANAT active site appears not to accommodate positively charged linkers as well as neutral ones; and (iv) substrate amine pK(a) depression may constitute one strategy for AANAT substrate recognition and catalysis. The results reported here have enhanced our understanding of AANAT substrate recognition/catalysis, and are important for novel inhibitor design. Since AANAT belongs to the GCN5-related N-acetyltransferase (GNAT) superfamily, our experimental strategies should find applications for other acetyltransferases. (C) 2003 Elsevier Science (USA). All rights reserved.

  DOI：

  10.1016/s0045-2068(03)00081-6
• 作为产物：
  描述：

  吲哚 、 戊二酸酐 在 magnesium 、 碘乙烷 作用下， 以 苯甲醚 为溶剂， 生成 5-indol-3-yl-5-oxo-pentanoic acid
  参考文献：
  名称：

  Novel bisubstrate analog inhibitors of serotonin N-acetyltransferase: the importance of being neutral

  摘要：

  [GRAPHICS]Linker modified novel bisubstrate analog inhibitors 4-7 for serotonin N-acetyltransferase (arylalkylamine N-acetyltransferase, AANAT) have been designed and synthesized. Examination of these inhibitors with AANAT in vitro suggested that: (i) linker hydrogen bonding makes only modest contributions to the affinity of bisubstrate analog inhibitors studied; (ii) greater than or equal to four methylene groups between the indole and the coenzyme A (CoASH) moieties are required for a bisubstrate analog inhibitor to achieve strong AANAT inhibition; (iii) the AANAT active site appears not to accommodate positively charged linkers as well as neutral ones; and (iv) substrate amine pK(a) depression may constitute one strategy for AANAT substrate recognition and catalysis. The results reported here have enhanced our understanding of AANAT substrate recognition/catalysis, and are important for novel inhibitor design. Since AANAT belongs to the GCN5-related N-acetyltransferase (GNAT) superfamily, our experimental strategies should find applications for other acetyltransferases. (C) 2003 Elsevier Science (USA). All rights reserved.

  DOI：

  10.1016/s0045-2068(03)00081-6

文献信息

• The action of acetic anhydride on N-methyltryptophans
  作者：A. N. Kost、T. V. Koronelli、R. S. Sagitullin

  DOI：10.1007/bf01134240

  日期：1966.5

  SummaryDepending on the reaction conditions, acetylation of the methylamino acid dl-abrine and 5-methoxy-dl-abrine gives acetylamino acids, acetyl dipeptides, and more complex compounds of the peptide type.

  总结取决于反应条件，甲基氨基酸 dl-abrine 和 5-甲氧基-dl-abrine 的乙酰化产生乙酰氨基酸、乙酰二肽和更复杂的肽类型化合物。
• KOST A. N.; YUROVSKAYA M. A.; NGUEN MIN TXAO, XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1975, HO 11, 1512-1517
  作者：KOST A. N.、 YUROVSKAYA M. A.、 NGUEN MIN TXAO

  DOI：——

  日期：——