芴甲氧羰基-DL-2-氨基丁酸 | 174879-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 芴甲氧羰基-DL-2-氨基丁酸
• 中文别名: Fmoc-DL-2-氨基丁酸；N-FMOC-2-氨基丁酸；N-Fmoc-2-氨基丁酸；FMOC-DL-2-氨基丁酸
• 英文名称: N-α-Fmoc-norvaline
• 英文别名: 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)butanoic acid；Fmoc-γ-abu-COOH；2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid；N-Fmoc-DL-2-amino-n-butyric acid；(+/-)-N-FMOC-α-aminobutyric acid；Fmoc-DL-2-aminobutyric acid；2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid
• CAS: 174879-28-8
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: XQIRYUNKLVPVRR-UHFFFAOYSA-N

物化性质

• 沸点：
  550.7±33.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  芴甲氧羰基-DL-2-氨基丁酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三异丙基硅烷 、 三氟乙酸 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(2-aminobutanoyl)aminoethanol
  参考文献：
  名称：

  Dipeptide alcohol-based inhibitors of eukaryotic DNA polymerase α

  摘要：

  We reported previously that a novel dipeptide alcohol, L-homoserylaminoethanol (Hse-Gly-ol), is a selective inhibitor of eukaryotic DNA polymerase epsilon (pol epsilon) [Bioorg. Med. Chem. 2004, 12, 957-962]. The discovery suggests that the dipeptide structure could be a chemical frame for a DNA polymerase inhibitor. Therefore, we chemically synthesized 27 different species of dipeptide alcohols, and tested this inhibitory capability. Compound 6 (L-aspartylaminoethanol, Asp-Gly-ol) was found to be the strongest pol alpha inhibitor. Compound 6 did not influence the activities of other replicative DNA polymerases such as delta and epsilon, and had no effect on the activities of prokaryotic DNA polymerases, nor DNA metabolic enzymes such as human immunodeficiency virus type I reverse transcriptase, T7 RNA polymerase and bovine deoxyribonuclease I. The inhibitory effect of compound 6 on pol alpha was dose-dependent, and 50% inhibition was observed at a concentration of 33.5 mu M. Compound 6-induced inhibition of pol alpha activity was noncompetitive with both the DNA template-primer and the dNTP substrate. This is the first report on a water-soluble pol alpha-specific inhibitor, sought for precise biochemical studies of pol alpha. The relationships between the structures of dipeptide alcohols and the inhibition of eukaryotic DNA polymerases are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.052
• 作为产物：
  描述：

  N-α-Fmoc-threonine benzyl ester 在 palladium on activated charcoal 吡啶 、 氢气 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 芴甲氧羰基-DL-2-氨基丁酸
  参考文献：
  名称：

  DEHYDRATION OF THREONINE ESTERS DURING TOSYLATION

  摘要：

  Tosylation of N-alpha -protected threonine methyl-and benzyl esters was investigated. Depending on the protecting groups, the composition of the reaction mixtures showed different ratio between O-tosyl-and dehydrothreonine derivatives. The latter was formed exclusively in case of N-alpha -Fmoc-threonine benzyl ester.

  DOI：

  10.1081/scc-100107012

文献信息

• The Asymmetric Synthesis of Amines via Nickel-Catalyzed Enantioconvergent Substitution Reactions
  作者：Ze-Peng Yang、Dylan J. Freas、Gregory C. Fu

  DOI：10.1021/jacs.0c13034

  日期：2021.2.24

  dialkyl carbinamines do not provide general access to amines wherein the two alkyl groups are of similar size (e.g., CH2R versus CH2R1). Herein, we report two mild methods for the catalytic enantioconvergent synthesis of protected dialkyl carbinamines, both of which use a chiral nickel catalyst to couple an alkylzinc reagent (1.1–1.2 equiv) with a racemic partner, specifically, an α-phthalimido alkyl chloride

  手性二烷基卡宾胺在有机化学、药物化学和生物化学等领域具有重要意义，例如用作生物活性分子、手性配体和手性催化剂。不幸的是，大多数用于合成二烷基卡宾胺的催化不对称方法不提供获得其中两个烷基具有相似大小的胺的一般途径（例如，CH 2 R与CH 2 R 1 ）。在此，我们报道了两种催化对映异构合成受保护的二烷基卡宾胺的温和方法，这两种方法都使用手性镍催化剂将烷基锌试剂（1.1-1.2当量）与外消旋伙伴偶联，特别是α-邻苯二甲酰亚氨基烷基氯或受保护的 α-氨基酸的N-羟基邻苯二甲酰亚胺 (NHP) 酯。该方法用途广泛，可提供带有一系列官能团的二烷基卡宾胺衍生物。对于NHP酯的偶联，我们进一步描述了一种一锅变体，其中NHP酯原位生成，允许从市售氨基酸衍生物一步生成对映体富集的受保护的二烷基卡宾胺；我们通过将其应用于一系列有趣的目标分子的有效催化对映选择性合成来证明该方法的实用性。
• Structural and mechanistic insights into the inhibition of amyloid-β aggregation by Aβ39-42 fragment derived synthetic peptides
  作者：Akshay Kapadia、Krishna K. Sharma、Indresh Kumar Maurya、Varinder Singh、Madhu Khullar、Rahul Jain

  DOI：10.1016/j.ejmech.2020.113126

  日期：2021.2

  permeability and offered proteolytic stability to the synthetic peptides. Several peptides exhibited promising protection against Aβ aggregation-mediated-neurotoxicity in PC-12 cells at doses ranged between 10 μM and 0.1 μM, further confirmed by the thioflavin-T fluorescence assay. CD study illustrate that these peptides restrict the β-sheet formation, and the non-appearance of Aβ42 fibrillar structures in

  淀粉样-β（Aβ）聚集的抑制是治疗阿尔茨海默氏病（AD）的有前途的方法。合成了基于亲本Aβ肽的Aβ39-42 C末端片段的38个四肽。使用非天然氨基酸的顺序替换/修饰赋予了支架多样性，增强的活性，增强的血脑屏障通透性并为合成肽提供了蛋白水解稳定性。硫黄素-T荧光测定进一步证实了几种肽在PC-12细胞中对Aβ聚集介导的神经毒性具有有希望的保护作用，剂量范围为10μM至0.1μM。CD研究表明，这些肽限制了β-折叠的形成以及Aβ42的不出现电镜中的原纤维结构证实了对Aβ42聚集的抑制。HRMS和ANS荧光光谱分析提供了更多的机理见解。两种选择的前导肽5和16表现出增强的血脑渗透性以及对血清和蛋白水解酶的稳定性。通过计算研究了在Aβ的单体和原纤维单元上的配体-Aβ相互作用的结构见解。前导肽的潜在抑制潜力和短序列为AD的肽衍生疗法的发展提供了新途径。
• Triaza- and tetraaza-anthracenedione derivates, their preparation and their use as pharmaceuticals
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1471066A1

  公开（公告）日：2004-10-27

  The present invention relates to triaza- and tetraaza-anthracenedione derivatives of the formula I, in which A, B and R1 to R5 have the meanings indicated in the claims. The compounds of formula I are valuable pharmacologically active compounds. They are useful in the treatment of various disease states including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency. They upregulate the expression of the enzyme endothelial nitric oxide (NO) synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention furthermore relates to processes for the preparation of compounds of the formula I, their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.

  本发明涉及式I的三氮杂和四氮杂蒽醌衍生物，其中A、B和R1至R5具有权利要求中所示的含义。式I的化合物是有价值的药理活性化合物。它们在治疗各种疾病状态中具有用处，包括心血管疾病，如动脉粥样硬化、血栓形成、冠状动脉疾病、高血压和心脏功能不全。它们上调内皮一氧化氮（NO）合酶的表达，并可应用于需要增加该酶的表达或增加NO水平或恢复降低的NO水平的情况。此外，本发明还涉及制备式I化合物的方法，它们的用途，特别是作为药物中的活性成分，以及包含它们的药物制剂。
• [EN] ESTROGEN RECEPTOR MODULATORS<br/>[FR] MODULATEURS DU RÉCEPTEUR DES ŒSTROGÈNES
  申请人：KALYRA PHARMACEUTICALS INC

  公开号：WO2017172957A1

  公开（公告）日：2017-10-05

  Compounds of Formula (I) are estrogen receptor alpha modulators, where the variables in Formula (I) are described in the disclosure. Such compounds, as well as pharmaceutically acceptable salts and compositions thereof, are useful for treating diseases or conditions that are estrogen receptor alpha dependent and/or estrogen receptor alpha mediated, including conditions characterized by excessive cellular proliferation, such as breast cancer.

  化合物的化学式（I）是雌激素受体α调节剂，其中化学式（I）中的变量在披露中有描述。这些化合物以及其药学上可接受的盐和组合物对于治疗依赖雌激素受体α和/或由雌激素受体α介导的疾病或症状是有用的，包括由细胞过度增殖所特征化的疾病，如乳腺癌。
• [EN] PYRROLOTRIAZINONE COMPOUNDS AND THEIR USE TO TREAT DISEASES<br/>[FR] COMPOSES DE PYRROLOTRIAZINONE ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003099286A1

  公开（公告）日：2003-12-04

  The present invention provides compounds of Formula (I), and pharmaceutically acceptable salts thereof useful for inducing mitotic arrest thereby making them useful as anti-cancer agents and other diseases which can be treated by inducing mitotic arrest.

  本发明提供了式（I）的化合物及其药学上可接受的盐，用于诱导有丝分裂阻滞，从而使其作为抗癌药物和其他可以通过诱导有丝分裂阻滞来治疗的疾病有用。