4(S)-butoxycarbonylamino-4-(methoxymethylcarbamoyl)butyric acid tert-butyl ester | 194985-20-1

• 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: 4(S)-butoxycarbonylamino-4-(methoxymethylcarbamoyl)butyric acid tert-butyl ester
• 英文别名: (S)-tert-butyl 4-(tert-butoxycarbonylamino)-5-(methoxy(methyl)amino)-5-oxopentanoate；tert-butyl N2-(tert-butoxycarbonyl)-N1-methoxy-N1-methyl-L-α-glutaminate；tert-butyl (4S)-5-[methoxy(methyl)amino]-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate
• CAS: 194985-20-1
• 化学式: C₁₆H₃₀N₂O₆
• 分子量: 346.424
• InChiKey: LBPAFPLMTXOZGT-NSHDSACASA-N

物化性质

• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4(S)-butoxycarbonylamino-4-(methoxymethylcarbamoyl)butyric acid tert-butyl ester 在 硫酸 、 三氟乙酸 、 potassium hydroxide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 醋酸叔丁酯 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 albogrisin A
  参考文献：
  名称：

  1 - N-甲基-3-甲基氨基-[ N-丁酸-3-（9-甲基-8-丙烯-7-一个）-酰胺]-苯并[ f ] [1的全合成和绝对构型的确定，7]萘啶-2-酮，一种新型苯并萘啶生物碱

  摘要：

  苯并萘啶生物碱的首次全合成（1）是一种从红树林衍生的链霉菌（Streptomyces albogriseolus）分离出的独特的二氮杂蒽烯生物碱。核心结构是通过几个关键的转变而明确构造的，例如Knoevenagel缩合，Curtius重排和环状氨基甲酸酯的形成-还原序列。手性的不饱和酮酸部分是从合成ñ -叔丁氧羰基-L-谷氨酸的γ-叔丁基酯（15）。确定绝对配置。

  DOI：

  10.1016/j.tetlet.2012.07.011
• 作为产物：
  描述：

  叔丁氧羰基-L-谷氨酸-5-叔丁酯 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 4(S)-butoxycarbonylamino-4-(methoxymethylcarbamoyl)butyric acid tert-butyl ester
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 2. Peptide Structure−Activity Studies

  摘要：

  The structure-based design, chemical synthesis, and biological evaluation of various peptide-derived human rhinovirus (HRV) 3C protease (3CP) inhibitors are described. These compounds are comprised of an ethyl propenoate Michael acceptor moiety and a tripeptidyl binding determinant. The systematic modification of each amino acid residue present in the binding determinant as well as the N-terminal functionality is described. Such modifications are shown to provide irreversible HRV-14 3CP inhibitors with anti-3CP activities (k(obs)/[I]) ranging from 60 to 280 000 M-1 s(-1) and antiviral EC50's which approach 0.15 mu M. An optimized inhibitor which incorporates several improvements identified by the structure-activity studies is also described. This molecule displays very rapid irreversible inhibition of HRV-14 3CP (k(obs)/[I] = 800 000 M-1 s(-1)) and potent antiviral activity against HRV-14 in cell culture (EC50 = 0.056 mu M). A 1.9 Angstrom crystal structure of an S-alkylthiocarbamate-containing inhibitor complexed with HRV-8 3CP is also detailed.

  DOI：

  10.1021/jm9800696

文献信息

• Heterocyclic Anti-Viral Compounds Comprising Metabolizable Moieties And Their Uses
  申请人：Singh Rajinder

  公开号：US20060247287A1

  公开（公告）日：2006-11-02

  The present invention relates to prodrugs and compositions thereof useful for treating or preventing Hepatitis C virus (HCV) infections. In particular, the present invention relates to prodrugs of substituted diphenyl-, diheteroaryl- and mixed phenyl heteroaryl substituted five-membered heterocycle compounds, compositions comprising the compounds and the use of such compounds and compositions to inhibit HCV replication and/or proliferation as a therapeutic approach towards the treatment and/or prevention of HCV infections in humans and animals.

  本发明涉及前药及其组合物，用于治疗或预防丙型肝炎病毒（HCV）感染。具体而言，本发明涉及取代二苯基、二杂环基和混合苯基杂环基取代的五元杂环化合物的前药，包含该化合物的组合物以及利用这些化合物和组合物来抑制HCV复制和/或增殖，作为治疗和/或预防人类和动物HCV感染的治疗方法。
• Identification of an α-Oxoamine Synthase and a One-Pot Two-Step Enzymatic Synthesis of α-Amino Ketones
  作者：Ting Zhou、Du Gao、Jia-Xin Li、Min-Juan Xu、Jun Xu

  DOI：10.1021/acs.orglett.0c03600

  日期：2021.1.1

  incorporation of l-glutamate to acyl-coenzyme A substrates. Combined with Alb29 and Mgr36 (an acyl-coenzyme A ligase), a one-pot enzymatic system was established to synthesize seven α-amino ketones. When these α-amino ketones were fed into the alb29 knockout strain Δalb29, respectively, the albogrisin analogs with different side chains were observed.

  Alb29 是一种 α-氧代胺合酶，参与Streptomyces albogriseolus MGR072中的 albogrisin 生物合成，被表征并负责将l-谷氨酸掺入酰基辅酶 A 底物。结合Alb29和Mgr36（一种酰基辅酶A连接酶），建立了一锅法合成七个α-氨基酮。当这些α-氨基酮分别加入alb29敲除菌株Δalb29时，观察到具有不同侧链的albogrisin类似物。
• Serine protease inhibitors
  申请人：Akzo Nobel, N.V.

  公开号：US06034067A1

  公开（公告）日：2000-03-07

  The invention relates to a compound having formula (I), wherein A, B, X, N, Z and Q are defined as described in the description. The compounds of the invention have anticoagulant activity and can be used in treating or preventing thrombin-related diseases. ##STR1##

  本发明涉及一种具有公式(I)的化合物，其中A、B、X、N、Z和Q的定义如描述中所述。该发明的化合物具有抗凝活性，可用于治疗或预防与凝血酶相关的疾病。 ##STR1##
• Heterocyclic anti-viral compounds comprising metabolizable moieties and their uses
  申请人：Rigel Pharmaceuticals, Inc.

  公开号：US07498353B2

  公开（公告）日：2009-03-03

  The present invention relates to prodrugs and compositions thereof useful for treating or preventing Hepatitis C virus (HCV) infections. In particular, the present invention relates to prodrugs of substituted diphenyl-, diheteroaryl- and mixed phenyl heteroaryl substituted five-membered heterocycle compounds, compositions comprising the compounds and the use of such compounds and compositions to inhibit HCV replication and/or proliferation as a therapeutic approach towards the treatment and/or prevention of HCV infections in humans and animals.

  本发明涉及一种用于治疗或预防丙型肝炎病毒（HCV）感染的前药和其组合物。具体而言，本发明涉及取代二苯基、二杂芳基和混合苯杂芳基取代的五元杂环化合物的前药，以及包含该化合物的组合物和使用该化合物和组合物来抑制HCV复制和/或增殖作为治疗和/或预防人类和动物HCV感染的治疗方法。
• WO2006/61714
  申请人：——

  公开号：——

  公开（公告）日：——