tert-butyl (S)-(3-(4-hydroxyphenyl)-1-((4-hydroxyphenyl)amino)-1-oxopropan-2-yl)carbamate | 179631-33-5

• 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: tert-butyl (S)-(3-(4-hydroxyphenyl)-1-((4-hydroxyphenyl)amino)-1-oxopropan-2-yl)carbamate
• 英文别名: tert-butyl N-[(2S)-1-(4-hydroxyanilino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamate
• CAS: 179631-33-5
• 化学式: C₂₀H₂₄N₂O₅
• 分子量: 372.421
• InChiKey: UGNCXQUVTAQZRL-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-(3-(4-hydroxyphenyl)-1-((4-hydroxyphenyl)amino)-1-oxopropan-2-yl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Design of novel tyrosine-nitrogen mustard hybrid molecules active against uterine, ovarian and breast cancer cell lines

  摘要：

  L-para-Tyrosine was linked to ortho-hydroxyaniline, meta-hydroxyaniline and para-hydroxyaniline giving three distinct tyrosinamide molecules. The new extended amino acid derivatives were constructed to imitate, in part, the estradiol (E-2, the natural female sex hormone) nucleus. The resulting tyrosinamides were then linked to chlorambucil either directly, or via a 5 and 10 carbon atoms spacer chain. This was done in an attempt to target cancerous cells expressing the estrogen receptor alpha (ER alpha) and to obtain a more specific chemotherapeutic agent. The tyrosinamide-chlorambucil molecules were designed and synthesized in good yields, according to two different approaches. The novel compounds were evaluated for their anticancer efficacy in hormone-dependent and hormone-independent (ER+; MCF-7 and ER-; MDA-MB-231) breast cancer cell lines. Interestingly, the meta-hydroxyphenyl-tyrosinamide-chlorambucil derivatives were more active than the ortho- and para- analogs. The molecules bearing a 5 carbon atoms spacer were selected for additional biological study using a panel of female cancerous cells; breast (ZR-75-1, MDA-MB-436, MDA-MB-468), ovarian (OVCAR-3, A2780) and uterine (Ishikawa, HEC-1A). It was discovered that for breast cancer cells, the new compounds were up to 4.2 times more active than chlorambucil itself. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.12.021
• 作为产物：
  描述：

  Boc-L-酪氨酸 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 tert-butyl (S)-(3-(4-hydroxyphenyl)-1-((4-hydroxyphenyl)amino)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  [EN] ANTICANCER AGENTS BASED ON AMINO ACID DERIVATIVES
  [FR] AGENTS ANTICANCÉREUX À BASE DE DÉRIVÉS D'ACIDES AMINÉS

  摘要：

  本发明提供了以下式（I）的化合物：其中T是L或-A-NH-C（O）-L-；L是-(CH2)n-或-(CH2)p-Z-；A是-(CH2)m-或天然氨基酸的烷基成分；R是-CO2R1，-CH2OH，-C（O）NH（羟基苯基）或C（S）NH（羟基苯基）；R1是H或是C1-C12烷基；X是-OH，OSO2R2，-Cl，-Br或-I；R2是C1-C12烷基或-CF3；Z是苯基或萘基；m是具有值1至20的整数；n是具有值1至20的整数；p是具有值1至20的整数或其对映体，非对映异构体，混合物，药用可接受的盐，溶剂化合物或前药。这些化合物可以用作抗癌剂。

  公开号：

  WO2011011865A1

文献信息

• Novel pyrrole based CB2 agonists: New insights on CB2 receptor role in regulating neurotransmitters' tone
  作者：Simone Di Micco、Tania Ciaglia、Emanuela Salviati、Perrone Michela、Magdalena Kostrzewa、Simona Musella、Aniello Schiano Moriello、Veronica Di Sarno、Gerardina Smaldone、Francesca Di Matteo、Ilaria Capolupo、Rosmara Infantino、Giuseppe Bifulco、Giacomo Pepe、Eduardo M. Sommella、Poulami Kumar、Manuela Giovanna Basilicata、Marco Allarà、Nuria Sánchez-Fernández、Ester Aso、Isabel M. Gomez-Monterrey、Pietro Campiglia、Carmine Ostacolo、Sabatino Maione、Alessia Ligresti、Alessia Bertamino

  DOI：10.1016/j.ejmech.2024.116298

  日期：2024.4

  inflammation, and psychiatric diseases. Recently, the CB2 receptor has gained increased attention considering its crucial role in modulating neuroinflammation in several pathological conditions like neurodegenerative diseases. Here we describe the rational design of pyrrole-based analogues, which led to a potent and pharmacokinetically suitable CB2 full agonist particularly effective in improving cognitive

  大麻素系统是研究最多的神经调节系统之一，因为它涉及多种病理学，例如癌症、炎症和精神疾病。最近，考虑到 CB2 受体在调节神经退行性疾病等多种病理状况中的神经炎症中的关键作用，它受到了越来越多的关注。在这里，我们描述了基于吡咯的类似物的合理设计，该类似物产生了一种有效且药代动力学合适的 CB2 完全激动剂，在改善东莨菪碱诱导的遗忘症小鼠模型中的认知功能方面特别有效。因此，我们通过研究这个实验范式中 CB2 激活和神经传递之间的相互关系来扩展我们的研究。为此，我们对小鼠大脑进行了 MALDI 成像分析，观察到给予我们的先导化合物能够恢复东莨菪碱对不同神经递质音调（例如乙酰胆碱、血清素和 GABA）的影响，从而揭示了重要的网络到目前为止，已经完全探索过了。
• [EN] ANTICANCER AGENTS BASED ON AMINO ACID DERIVATIVES<br/>[FR] AGENTS ANTICANCÉREUX À BASE DE DÉRIVÉS D'ACIDES AMINÉS
  申请人：3R VALO S E C

  公开号：WO2011011865A1

  公开（公告）日：2011-02-03

  The present invention provides compounds of formula (I): in which T is L or -A-NH-C(O)-L-; L is -(CH2)n- or -(CH2)p-Z-; A is -(CH2)m- or an alkyl component of a naturally occurring amino acid; R is -CO2R1, -CH2OH, -C(O)NH(hydroxyphenyl) or C(S)NH(hydroxyphenyl); R1 is H or is C1-C12 alkyl; X is -OH, OSO2R2, -Cl, -Br, or -I; R2 is C1-C12 alkyl or -CF3; Z is phenyl or naphthyl; m is an integer having a value of 1 to 20; n is an integer having a value of 1 to 20; and p is an integer having a value of 1 to 20 or an enantiomer, diastereoisomer, racemic mixture, pharmaceutically acceptable salt, solvate or prodrug thereof. These compounds can be useful as anticancer agents.

  本发明提供了以下式（I）的化合物：其中T是L或-A-NH-C（O）-L-；L是-(CH2)n-或-(CH2)p-Z-；A是-(CH2)m-或天然氨基酸的烷基成分；R是-CO2R1，-CH2OH，-C（O）NH（羟基苯基）或C（S）NH（羟基苯基）；R1是H或是C1-C12烷基；X是-OH，OSO2R2，-Cl，-Br或-I；R2是C1-C12烷基或-CF3；Z是苯基或萘基；m是具有值1至20的整数；n是具有值1至20的整数；p是具有值1至20的整数或其对映体，非对映异构体，混合物，药用可接受的盐，溶剂化合物或前药。这些化合物可以用作抗癌剂。
• Design of novel tyrosine-nitrogen mustard hybrid molecules active against uterine, ovarian and breast cancer cell lines
  作者：Caroline Descôteaux、Kevin Brasseur、Valérie Leblanc、Sophie Parent、Éric Asselin、Gervais Bérubé

  DOI：10.1016/j.steroids.2011.12.021

  日期：2012.4

  L-para-Tyrosine was linked to ortho-hydroxyaniline, meta-hydroxyaniline and para-hydroxyaniline giving three distinct tyrosinamide molecules. The new extended amino acid derivatives were constructed to imitate, in part, the estradiol (E-2, the natural female sex hormone) nucleus. The resulting tyrosinamides were then linked to chlorambucil either directly, or via a 5 and 10 carbon atoms spacer chain. This was done in an attempt to target cancerous cells expressing the estrogen receptor alpha (ER alpha) and to obtain a more specific chemotherapeutic agent. The tyrosinamide-chlorambucil molecules were designed and synthesized in good yields, according to two different approaches. The novel compounds were evaluated for their anticancer efficacy in hormone-dependent and hormone-independent (ER+; MCF-7 and ER-; MDA-MB-231) breast cancer cell lines. Interestingly, the meta-hydroxyphenyl-tyrosinamide-chlorambucil derivatives were more active than the ortho- and para- analogs. The molecules bearing a 5 carbon atoms spacer were selected for additional biological study using a panel of female cancerous cells; breast (ZR-75-1, MDA-MB-436, MDA-MB-468), ovarian (OVCAR-3, A2780) and uterine (Ishikawa, HEC-1A). It was discovered that for breast cancer cells, the new compounds were up to 4.2 times more active than chlorambucil itself. (C) 2011 Elsevier Inc. All rights reserved.