CBZ-7-氨基庚酸 | 23434-37-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: CBZ-7-氨基庚酸
• 英文名称: 7-(((benzyloxy)carbonyl)amino)heptanoic acid
• 英文别名: 7‐{[(benzyloxy)carbonyl]amino}heptanoic acid；7-{[(Benzyloxy)carbonyl]amino}heptanoic acid；7-(phenylmethoxycarbonylamino)heptanoic acid
• CAS: 23434-37-9
• 化学式: C₁₅H₂₁NO₄
• mdl: MFCD09930580
• 分子量: 279.336
• InChiKey: XBVBOABWPAYAFH-UHFFFAOYSA-N

物化性质

• 熔点：
  174-178 °C
• 沸点：
  477.6±38.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.466
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  CBZ-7-氨基庚酸 在 palladium on activated charcoal 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 甲醇 、 乙二醇甲醚 、 水 、 溶剂黄146 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 5.0h， 生成
  参考文献：
  名称：

  Use of adenine nucleotide derivatives to assess the potential of exo-active-site-directed reagents as species- or isozyme-specific enzyme inactivators. 3. Synthesis of adenosine 5'-triphosphate derivatives with N6- or 8-substituents bearing iodoacetyl groups

  摘要：

  Several series of N6- or 8-substituted derivatives of adenosine 5'-triphosphate (ATP) were synthesized. N6-(omega-Aminoalkyl) derivatives of adenosine 5'-monophosphate (AMP) were converted into their omega-N-carbobenzyloxy derivatives, and these were converted, via the 2',3'-O-carbonyl derivatives of their 5'-phosphorimidazolidates, into the corresponding ATP derivatives. Hydrogenolytic removal of the carbobenzyloxy groups, followed by iodoacetylation of the omega-amino groups with N-(iodoacetoxy)succinimide, gave N6-R-ATP, where R = (CH2)nNHCOCH2I (n = 2--8) or (CH2)nCON)CH3)(CH2)mN(CH3)CO(CH2)nNHCOCH2I (n = m = 3; n = 3, m = 4; n = 4, m = 3; n = m = 4). Condensation of N6-(omega-aminoalkyl) derivatives of AMP with N-hydroxysuccinimide esters of omega-[N-(carbobenzyloxy)amino] carboxylic acids gave N6-(CH2)nNHCO(CH2)mNH-Cbz derivatives of AMP which, upon conversion to the corresponding derivatives of ATP, followed by removal of the carbobenzyloxy group and iodoacetylation, as described above, gave N6-(CH2)nNHCO(CH2)mNHCOCH2I-ATP derivatives (n = 3, m = 5 or 6; n = 4, m = 5; n = 6, m = 1--6). The same sequence of reactions starting with N6-[omega-(methylamino)alkyl] derivatives of N6-CH3-AMP gave N6-CH3, N6-(CH2)nH(CH3)CO(CH2)mNHCOCH2I derivatives of ATP (n = 4, m = 3, 5 or 6; n = 6, m = 5 or 6). Reaction of alpha, omega-diaminoalkanes with 8-Br-ATP gave 8-NH(CH2)nNH2 derivatives of ATP, which upon iodoacetylation gave 8-NH(CH2)nNHCOCH2I derivatives of ATP (n = 2, 4, 6, or 8). Substrate and inhibitor properties indicated that the ATP derivatives are potential exco-ATP-site-directed inactivators of hexokinases, adenylate kinases, and pyruvate kinases.

  DOI：

  10.1021/jm00346a009
• 作为产物：
  描述：

  氯甲酸苄酯 在 正丁基锂 、 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.67h， 生成 CBZ-7-氨基庚酸
  参考文献：
  名称：

  通过酰胺选择性还原亲核加成法全合成（±）-地球毒素

  摘要：

  已开发出一种化学选择性的方法，可以完全合成（±）-地理毒素。成功的关键是利用N-甲氧基酰胺，它可以使酰胺与醛直接偶联，并在存在各种敏感和亲电子官能团（例如甲酯）的情况下，将酰胺选择性还原性亲核加成到酰胺上。这种化学选择性方法最大程度地减少了保护基操纵和氧化还原反应的使用，从而实现了迄今为止描述的最简洁，最有效的（±）-地球毒毒素的全合成。

  DOI：

  10.1002/anie.201308905

文献信息

• Combined inhibition of the EGFR/AKT pathways by a novel conjugate of quinazoline with isothiocyanate
  作者：Andrea Tarozzi、Chiara Marchetti、Benedetta Nicolini、Massimo D'Amico、Nicole Ticchi、Letizia Pruccoli、Vincenzo Tumiatti、Elena Simoni、Alessio Lodola、Marco Mor、Andrea Milelli、Anna Minarini

  DOI：10.1016/j.ejmech.2016.04.002

  日期：2016.7

  functions of cancer cells. According to these considerations, a series of multitarget molecules have been designed by combining key structural features derived from an EGFR-TKI, PD168393, and the isothiocyanate sulforaphane. Among the obtained molecules 1–6, compound 6 emerges as a promising lead compound able to exert antiproliferative and proapoptotic effects in A431 epithelial cancer cell line by covalently

  表皮生长因子受体抑制剂（EGFR-TKIs）代表了广泛用于抗癌治疗的一类化合物。越来越多的研究报道了联合疗法，其中EGFR-TK活性的阻断与其下游通路（如PI3K-Akt）的抑制有关。萝卜硫烷靶向PI3K-Akt途径，该途径的失调与癌细胞的许多功能有关。根据这些考虑，通过结合衍生自EGFR-TKI，PD168393和异硫氰酸酯萝卜硫烷的关键结构特征，设计了一系列多目标分子。在获得的分子1 - 6，化合物6 它作为一种有前途的先导化合物出现，能够通过与EGFR-TK共价结合并在不影响总Akt水平的情况下降低Akt的磷酸化，从而在A431上皮癌细胞系中发挥抗增殖和促凋亡作用。
• [EN] PDE4 INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND THERAPEUTIC APPLICATIONS<br/>[FR] INHIBITEURS DE PDE4, COMPOSITIONS PHARMACEUTIQUES ET APPLICATIONS THÉRAPEUTIQUES
  申请人：BIOTHERYX INC

  公开号：WO2021119571A1

  公开（公告）日：2021-06-17

  Provided herein are phosphodiesterase 4 (PDE4) inhibitors, e.g., a compound of Formula (I) or (II), and pharmaceutical compositions thereof. Also provided herein are methods of their use for treating, preventing, or ameliorating one or more symptoms of a disease, disorder, or condition associated with PDE4 malfunction.

  提供的是磷酸二酯酶4（PDE4）抑制剂，例如，公式（I）或（II）的化合物，以及它们的药物组合物。还提供了使用它们来治疗、预防或改善与PDE4功能障碍相关的一种或多种疾病、紊乱或症状的方法。
• Chemoselective Reductive Nucleophilic Addition to Tertiary Amides, Secondary Amides, and<i>N</i>-Methoxyamides
  作者：Minami Nakajima、Yukiko Oda、Takamasa Wada、Ryo Minamikawa、Kenji Shirokane、Takaaki Sato、Noritaka Chida

  DOI：10.1002/chem.201404648

  日期：2014.12.22

  modern organic synthesis, chemoselectivity is recognized as an important factor in the development of new methodologies. Chemoselective nucleophilic addition to amide carbonyl centers is a challenge because classical methods require harsh reaction conditions to overcome the poor electrophilicity of the amide carbonyl group. We have successfully developed a reductive nucleophilic addition of mild nucleophiles

  随着目标分子在现代有机合成中的复杂性增加，化学选择性被认为是开发新方法的重要因素。酰胺羰基中心的化学选择性亲核加成是一个挑战，因为经典方法需要苛刻的反应条件以克服酰胺羰基的不良亲电性。我们已经成功开发出使用Schwartz试剂将温和的亲核试剂还原性添加到叔酰胺，仲酰胺和N-甲氧基酰胺上的亲核试剂[Cp 2ZrHCl]。该反应在各种敏感的官能团，例如甲酯的存在下，以高度化学选择性的方式发生，这些官能团通常需要在亲核加成之前进行保护。该反应将适用于由容易获得的酰胺基团简单合成复杂的天然生物碱。
• Amino-acids and peptides. Part IX. Some neighbouring-group amino–amide and hydroxy–amide interactions
  作者：Jacquita A. Davies、C. H. Hassall、I. H. Rogers

  DOI：10.1039/j39690001358

  日期：——

  Base-catalysed hydrolysis studies have provided evidence of neighbouring-group amino–amide interactions in compounds with the formulae H2N·[CH2]x·CO·NHMe (x= 3, 4, or 5), and in 6-aminodecane-10-lactam. Acid-catalysed hydrolysis studies have indicated that transannular hydroxy-amide interactions occur with 4-hydroxyhexane-6-lactam, 5-hydroxyoctane-8-lactam, and 6-hydroxydecane-10-lactam. The mechanisms

  碱催化的水解研究提供了在具有以下化学式的化合物H 2 N·[CH 2 ] x ·CO·NHMe（x = 3、4、5）和6-氨基癸烷中相邻基团氨基酰胺相互作用的证据。-10-内酰胺 酸催化的水解研究表明，环戊基羟基酰胺相互作用与4-羟基己烷-6-内酰胺，5-羟基辛烷-8-内酰胺和6-羟基癸烷-10-内酰胺发生。讨论了这些反应的机理以及此类过程在肽化学中的意义。
• Bridged isocytosine-adenosine compounds: Synthesis and antibacterial evaluation
  作者：O. William Lever、B. Randall Vestal

  DOI：10.1002/jhet.5570230348

  日期：1986.5

  In an approach to novel antibacterial agents, we synthesized a series of 5-nitrosoisocytosines in which a 6-alkylamino substituent is bridged, through an amide linkage at the terminus of the alkyl chain, to the 5′-position of a 5′-deoxyadenosine moiety. A corresponding series of 5-nitro analogues were also prepared. None of the bridged compounds showed significant antibacterial activity.

  在一种新型抗菌剂的方法中，我们合成了一系列5-亚硝基异胞嘧啶，其中6-烷基氨基取代基通过烷基链末端的酰胺键桥接至5'-脱氧腺苷的5'-位部分。还制备了相应的5-硝基类似物系列。没有一种桥接化合物显示出明显的抗菌活性。