Boc-γ-aminobutyryl-glycine ethyl ester | 111819-21-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Boc-γ-aminobutyryl-glycine ethyl ester
• 英文别名: (4tert-Butoxycarbonylamino-butyrylamino)-acetic Acid Ethyl Ester；Ethyl 2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoylamino]acetate
• CAS: 111819-21-7
• 化学式: C₁₃H₂₄N₂O₅
• mdl: MFCD24391497
• 分子量: 288.344
• InChiKey: HWAWVAVFJFJNNA-UHFFFAOYSA-N

物化性质

• 沸点：
  450.9±25.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.769
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-γ-aminobutyryl-glycine ethyl ester 在 lithium hydroxide 作用下， 以78%的产率得到(4-tert-Butoxycarbonylamino-butyrylamino)-acetic Acid
  参考文献：
  名称：

  Total Synthesis of Bleomycin A2 and Related Agents. 1. Synthesis and DNA Binding Properties of the Extended C-Terminus: Tripeptide S, Tetrapeptide S, Pentapeptide S, and Related Agents

  摘要：

  Full details of concise, diastereocontrolled syntheses of 2-5 and their incorporation into tri-, tetra-, and pentapeptide S, the C-terminus of bleomycin Alt are described. The extension of the studies to the synthesis of a complete set of tri- and tetrapeptide S structural analogs 29a,b and 43b-j is detailed, and their DNA binding constants (apparent K-B, calf thymus DNA) and apparent binding site sizes were determined. Consistent with past observations, the studies highlight the fact that the majority of the DNA binding affinity for bleomycin A(2) (1.0 X 10(5) M(-1)) and deglycobleomycin Aa (1.1 x 10(5) M(-1)) is embodied within N-BOC-tripeptide S (0.26 X 10(5) M(-1)). The additional comparisons of 29a (O.18 x 10(5) M(-1)), N-BOC-tetrapeptide S (0.21 x 10(5) M(-1)), 43h (0.20 x 10(5) M(-1)), and N-BOC-pentapeptide S (0.23 X 10(5) M(-1)) versus N-BOC-dipeptide S (0.10 x 10(5) M(-1)) indicate productive stabilizing binding interactions for the tripeptide S L-threonine subunit and substituent, illustrate that the entire pentanoic acid subunit of tetrapeptide S and its substituents do not significantly contribute to DNA binding affinity, and indicate that the entire beta-hydroxy-L-histidine subunit of pentapeptide S does not contribute to DNA binding affinity. With the exception of the L-threonine side chain substituent, the observations suggest that the tri- and tetrapeptide S substituent effects on the bleomycin A(2) DNA cleavage reaction are not due to substantial stabilizing binding interactions with duplex DNA. In addition, the measured apparent binding site sizes for bleomycin A(2)(3.8 base pairs), deglycobleomycin A(2) (3.9 base pairs), N-BOC-tripeptide S (3.6 base pairs), N-BOC-tetrapeptide S (3.7 base pairs), 43h (3.5 base pairs), and N-BOC-pentapeptide S (4.2 base pairs) versus N-BOC-dipeptide S (2.2 base pairs) and 29a (2.7 base pairs) suggest that it is the tripeptide S subunit of bleomycin A(2) that is fully bound to duplex DNA, that the tripeptide S L-threonine hydroxyethyl substituent detectably affects the agent interaction with duplex DNA, but that the presence or absence of the other tetrapeptide S and pentapeptide S backbone substituents do not substantially alter the binding site size or tripeptide S binding mode.

  DOI：

  10.1021/ja00092a011
• 作为产物：
  描述：

  甘氨酸乙酯盐酸盐 、 1-(叔丁氧羰基)-2-吡咯烷酮 在 三乙胺 作用下， 以 乙腈 为溶剂， 90.0 ℃ 、999.99 MPa 条件下， 反应 24.0h， 以87%的产率得到Boc-γ-aminobutyryl-glycine ethyl ester
  参考文献：
  名称：

  在高压条件下将内酰胺转化为ω-氨基羧酰胺的有效方法

  摘要：

  的高压反应Ñ与胺-Boc内酰胺提供了一种有效条目ω- Ñ -Boc氨基羧酰胺衍生物。

  DOI：

  10.1016/s0040-4039(00)61241-8

文献信息

• Structure–Activity Relationship and Mode of Action of <i>N</i>-(6-Ferrocenyl-2-naphthoyl) Dipeptide Ethyl Esters: Novel Organometallic Anticancer Compounds
  作者：Áine Mooney、Rachel Tiedt、Thamir Maghoub、Norma O’Donovan、John Crown、Blánaid White、Peter T. M. Kenny

  DOI：10.1021/jm3004027

  日期：2012.6.14

  In this article, we report the findings of a comprehensive structure–activity relationship study of N-(6-ferrocenyl-2-naphthoyl) dipeptide ethyl esters, in which novel analogues were designed, synthesized, and evaluated in vitro for antiproliferative effect. Two new compounds, 2 and 16, showed potent nanomolar activity in the H1299 NSCLC cell line, with exceptional IC50 values of 0.13 and 0.14 μM,

  在本文中，我们报告了N-（6-二茂铁基-2-萘甲酰基）二肽乙酯的全面结构-活性关系研究的结果，该研究设计，合成和评估了新的类似物在体外的抗增殖作用。两种新化合物2和16在H1299 NSCLC细胞系中均显示出强大的纳摩尔活性，其出色的IC 50值分别为0.13和0.14μM。还发现这些化合物在Sk-Mel-28恶性黑色素瘤细胞系中具有显着活性（IC 50值分别为1.10和1.06μM）。还进行了研究以阐明这些新型有机金属抗癌化合物的作用方式。H1299细胞系中的细胞周期分析表明，这些化合物可诱导细胞凋亡，而鸟嘌呤氧化研究证实2能够通过ROS介导的机制产生氧化损伤。
• US6117842
  申请人：——

  公开号：——

  公开（公告）日：——
• FIBRINOGEN RECEPTOR ANTAGONISTS
  申请人：MERCK & CO., INC.

  公开号：EP1061934A1

  公开（公告）日：2000-12-27
• US6117842A
  申请人：——

  公开号：US6117842A

  公开（公告）日：2000-09-12
• [EN] FIBRINOGEN RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DE RECEPTEUR FIBROGENE
  申请人：MERCK & CO., INC.

  公开号：WO1999045939A1

  公开（公告）日：1999-09-16

  (EN) Compounds of this invention have the formula: X-(CH2)n-C(O)NH-A-C(COOR5)R3R4 or a pharmaceutically acceptable salt thereof, e.g. formula (1-7) which are useful for inhibiting fibrinogen binding to blood platelets, thereby inhibiting platelet aggregation.(FR) L'invention concerne des composés représentés par la formule X-(CH2)n-C(O)NH-A-C(COOR5)R3R4 ou un sel pharmaceutiquement acceptable de ceux-ci représenté par la formule (1-7). Ces composés sont utiles pour inhiber un fibrogène se liant aux plaquettes sanguines, inhibant de ce fait une agrégation de plaquettes.