N-benzoyl-L-serine methyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzoyl-L-serine methyl ester
• 英文别名: methyl benzoyl-L-serinate；Bz-Ser-OMe；N-benzoylserine methyl ester；methyl (2S)-2-benzamido-3-hydroxypropanoate
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: OEWSGVFWOOIBLB-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzoyl-L-serine methyl ester 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 1.5h， 以74%的产率得到苯甲酰胺
  参考文献：
  名称：

  Protein Backbone Modification by Novel C.alpha.-C Side-Chain Scission

  摘要：

  alpha-Ketoamide (-NH-CO-CO-) units in intact peptides are generated from Ser/Thr residues via Ru(VIII)catalyzed C-alpha-C side-chain scission. Facets associated with this novel cu-carbon modification have been probed with 75 peptides chosen to represent every possible peptide environment. The reactions were carried out at room temperature with in situ generated Ru(VIII) in biphasic (CH3CN/CCl4/pH 3 phosphate buffer, 1:1:2 v/v) medium. Whereas Ser/Thr residues placed at the C-terminal end in peptides undergo N-C bond scission leading to des-Ser/Thr peptide amides-thus acting as Gly equivalents in simulating the alpha-amidating action of pituitary enzymes-those located at the N-terminal or nonterminal or even at the C-terminal position (protected as amide) were found to undergo oxidative C-C bond scission (involving C-alpha and C side-chain bond), resulting in the generation of alpha-ketoamide (-NH-CO-CO-) units in the intact peptide backbone. The difference in the products arising from C-alpha-C side-chain scission of Ser/Thr esters and amides is rationalized on the basis of a common mechanism involving either oxaloesters [Pep-NH-CO-COX; X = OMe] or oxalamides [X = NH2 or NH-Pep] arising from the oxidation of initially formed carbinolamide intermediates [Pep-NH-CH(OH)-COX],wherein, while the former are shown to undergo hydrolysis to terminal amides [Pep-NH2], the oxalamides are found to be stable to hydrolysis. Ancillary noteworthy findings are those of peptide bond scission when contiguous Ser-Ser/Thr-Thr residues are present and the oxidative cleavage at C-terminal Tyr/Trp sites generating des amides. The oxidative methodology presented here is mild, simple, and practical and proceeds with chiral retention. The insensitivity of a large number of amino acid residues, such as Gly, Ala, Leu, Asn, Gln, Asp, Glu, Pro, Arg, Phe, Lys, Val, and Aib, and N-protecting groups, such as Boc, Z, and Bz, toward Ru(VIII) under the experimental conditions should make this methodology practical and useful. Sulfur-containing amino acids Cys and Met get oxidized to sulfones in the products.

  DOI：

  10.1021/ja00094a008
• 作为产物：
  描述：

  苯甲酸 在 草酰氯 、 碳酸氢钠 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 N-benzoyl-L-serine methyl ester
  参考文献：
  名称：

  保留N-（2-苯基）苯甲酰基的5元脂环族α-氨基酸在光诱导丙烯腈脱羧分子间自由基中的手性

  摘要：

  在温和的有机光氧化还原催化条件下，将带有（2-苯基）苯甲酰基保护基的5元脂环族α-氨基酸的光诱导脱羧自由基加成到丙烯腈上，通过手性记忆（MOC），γ-氨基酸衍生物具有高度的手性保留能力战略。在光诱导的脱羧中手性的保留强烈依赖于脂环族α-氨基酸和烯烃的结构。据我们所知，这是使用MOC策略将烯烃脱羧分子间自由基加成至烯烃并在自由基生成位置保留手性的第一个例子。

  DOI：

  10.1016/j.tet.2019.130493

文献信息

• [EN] GRANZYME B DIRECTED IMAGING AND THERAPY<br/>[FR] IMAGERIE DU GRANZYME B ET THÉRAPIE DIRIGÉES CONTRE LE GRANZYME B
  申请人：CYTOSITE BIOPHARMA INC

  公开号：WO2019160916A1

  公开（公告）日：2019-08-22

  Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

  本文提供了用于成像Granzyme B的杂环化合物。还提供了成像Granzyme B的方法、联合疗法以及包含Granzyme B成像试剂的试剂盒。
• Toward the development of chemoprevention agents. Part 1: Design, synthesis, and anti-inflammatory activities of a new class of 2,5-disubstituted-dioxacycloalkanes
  作者：Keli Gu、Lanrong Bi、Ming Zhao、Chao Wang、Jingfang Ju、Shiqi Peng

  DOI：10.1016/j.bmc.2007.05.013

  日期：2007.7

  A new class of 2,5-disubstituted-dioxacycloalkanes were designed and synthesized via stereoselective synthetic method as cancer chemoprevention agents. The anti-inflammatory activities of these compounds were tested using the xylene-induced mouse ear edema model. Some of these compounds exhibited comparable or better anti-inflammatory activities than that of aspirin suggesting that they can be further

  设计并通过立体选择性合成方法合成了一类新的2,5-二取代-二氧杂环戊烷作为癌症的化学预防剂。使用二甲苯诱导的小鼠耳朵水肿模型测试了这些化合物的抗炎活性。这些化合物中的某些具有比阿司匹林更好的抗炎活性，这表明它们可以进一步发展为潜在的抗炎药先导化合物。另外，这些抗炎药的治疗并未延长小鼠的尾巴出血时间。还分析了这些化合物之间的结构/活性关系。
• 5-Benzoylamino-1,3-dioxacyclanes, the method for preparing the same and their use as PKC inhibitor
  申请人：Zen Hayley

  公开号：US20050043396A1

  公开（公告）日：2005-02-24

  The present invention discloses a series of benzoylamino-1,3-dioxacyclane compounds, of which compounds 1-21 were prepared via transacetalisation reaction between N-benzoylaminoglycol and 1,1,3,3-tetramethoxypropane; while compounds 22-48 were prepared via stereospecific acetalisation reaction between N-benzoylamino glycol and aromatic aldehyde, and if necessary, the nitro groups were reduced and further be salified with propane diacid and L-Arg or L-Lys. These compounds possess the structural type of PKC inhibitor and positive anti-inflammatory effect, and can be applied in medical fields as PKC inhibitor for corresponding therapy.

  本发明公开了一系列苯甲酰氨基-1,3-二氧杂环丁烷化合物，其中化合物1-21是通过N-苯甲酰氨基乙醇与1,1,3,3-四甲氧基丙烷之间的缩酮化反应制备的；而化合物22-48是通过N-苯甲酰氨基乙醇与芳香醛之间的立体特异性缩醛化反应制备的，如果有必要，可以将硝基还原，并进一步与丙烷二酸和L-精氨酸或L-赖氨酸成盐。这些化合物具有PKC抑制剂的结构类型和积极的抗炎效果，并且可以作为PKC抑制剂应用于医学领域的相应治疗。
• Synthesis of Substituted Oxazoles from<i>N</i>-Acyl-β-hydroxyamino Acid Derivatives
  作者：Paula M. T. Ferreira、Luís S. Monteiro、Goreti Pereira

  DOI：10.1002/ejoc.200800602

  日期：2008.9

  β-diiododehydroalanine derivatives. Although the reason for the different reactivities of the N-acyldehydroamino acids is not completely clear to us, cyclic voltammetry studies showed that the less-reactive derivatives have higher reduction potentials. This suggests that the double bonds in dehydroaminobutyric acid derivatives are more susceptible to electrophilic attack by iodine.(© Wiley-VCH Verlag GmbH & Co. KGaA

  制备了几种 N-酰基-β-羟基氨基酸，并在 4-（二甲氨基）吡啶存在下用二碳酸二叔丁酯处理，然后用 N,N,N',N'-四甲基胍处理，得到相应的N-酰基脱氢氨基酸的产率很高。然后用 I2/K2CO3 和 1,8-二氮杂双环 [5.4.0] undec-7-ene 处理这些。N-酰基脱氢氨基丁酸的甲酯以良好至高产率得到相应的取代恶唑。N-酰基脱氢苯丙氨酸与β-碘脱氢苯丙氨酸一起以低至中等产率得到5-苯基恶唑衍生物。在相同条件下，N-酰基脱氢丙氨酸不能得到相应的恶唑。然而，当反应在没有 DBU 的情况下进行时，可以分离出 β,β-二碘脱氢丙氨酸衍生物。尽管我们并不完全清楚 N-酰基脱氢氨基酸不同反应性的原因，但循环伏安法研究表明，反应性较低的衍生物具有更高的还原电位。这表明脱氢氨基丁酸衍生物中的双键更容易受到碘的亲电攻击。 (© Wiley-VCH Verlag GmbH & Co. KGaA
• Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
  申请人：——

  公开号：US20030236227A1

  公开（公告）日：2003-12-25

  The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

  该发明提供了在治疗2型糖尿病中有用的药物化合物。这些化合物具有优势，因为它们可以被代谢药物解毒系统迅速代谢。特别地，设计了包含酯基的噻唑烷二酮类似物的化合物。该发明还涉及治疗疾病的方法，如糖尿病，包括给予经设计为能够被血清或细胞内酯酶代谢的化合物的治疗有效组合物。还教授了含酯基的噻唑烷二酮类似物的药物组合物。