β-acetylthiopropionaldehyde | 53943-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-acetylthiopropionaldehyde
• 英文别名: S-(3-oxopropyl) ethanethioate；S-(3-oxopropyl)ethanethioate；S-3-oxopropyl ethanethioate；3-(acetylsulfanyl)propanal；S-3-oxopropyl thioacetate；3-acetylsulfanylpropanal
• CAS: 53943-93-4
• 化学式: C₅H₈O₂S
• 分子量: 132.183
• InChiKey: LLGHPZSANAZMFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  β-acetylthiopropionaldehyde 在 盐酸 、 sodium methylate 、 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 5-[3-(R,S)-3-(methoxycarbonylamino)-3-(phosphonopropyl)sulfanyl]pentanoic acid
  参考文献：
  名称：

  The development of a new class of inhibitors for betaine-homocysteine S-methyltransferase

  摘要：

  Betaine-homocysteine S-methyltransferase (BHMT) is an important zinc-dependent methyltransferase that uses betaine as the methyl donor for the remethylation of homocysteine to form methionine. In the liver, BHMT performs to half of the homocysteine remethylation. In this study, we systematically investigated the tolerance of the enzyme for modifications at the "homocysteine" part of the previously reported potent inhibitor (R,S)-5-(3-amino-3-carboxy-propylsulfanyl)-pentanoic acid (1). In the new compounds, which are S-alkylated homocysteine derivatives, we replaced the carboxylic group in the "homocysteine" part of inhibitor 1 with different isosteric moieties (tetrazole and oxadiazolone); we suppressed the carboxylic negative charge by amidations; we enhanced acidity by replacing the carboxylate with phosphonic or phosphinic acids; and we introduced pyrrolidine steric constraints. Some of these compounds display high affinity toward human BHMT and may be useful for further pharmacological studies of this enzyme. Although none of the new compounds were more potent inhibitors than the reference inhibitor 1, this study helped to completely define the structural requirements of the active site of BHMT and revealed the remarkable selectivity of the enzyme for homocysteine. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.039
• 作为产物：
  描述：

  丙烯醛 、 硫代乙酸 以80%的产率得到β-acetylthiopropionaldehyde
  参考文献：
  名称：

  作为选择性 A3 腺苷受体拮抗剂的 3,5-二酰基-2, 4-二烷基吡啶衍生物的合成、CoMFA 分析和受体对接。

  摘要：

  已发现 3,5-二酰基-2,4-二烷基-6-苯基吡啶衍生物是人和大鼠 A3 腺苷受体的选择性拮抗剂（Li 等人 J. Med. Chem. 1998, 41, 3186-3201） 。在本研究中，合成了该系列中的环约束、氟、羟基和其他衍生物，并在放射性配体结合测定中测试了对腺苷受体的亲和力。使用[125I]AB-MECA（N6-（4-氨基-3-碘苄基）-5'-N-甲基氨基甲酰基腺苷）测定重组人和大鼠A3腺苷受体的Ki值。确定 A3 腺苷受体的选择性与大鼠脑 A1 和 A2A 受体上放射性配体的结合，并确定吡啶环不同位置（3-和 5-酰基取代基以及 2-和 4-烷基取代基）的结构-活性关系探查。在 5 位包含 β-氟乙基 (7) 或 γ-氟丙酯 (26) 有利于人 A3 受体亲和力，导致 Ki 值分别为 4.2 和 9.7 nM，而五氟丙基类似物明显较低对人类 A3 受体有效。在 2、3 和

  DOI：

  10.1021/jm980550w

文献信息

• [EN] AMINOPEPTIDASE A INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME<br/>[FR] INHIBITEURS D'AMINOPEPTIDASE A ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT
  申请人：QUANTUM GENOMICS

  公开号：WO2020084131A1

  公开（公告）日：2020-04-30

  The present invention relates to a novel compound, to a composition comprising the same, to methods for preparing the compound, and the use of this compound in therapy. In particular, the present invention relates to compound that is useful in the treatment and prevention of primary and secondary arterial hypertension, ictus, myocardial ischaemia, cardiac and renal insufficiency, myocardial infarction, peripheral vascular disease, diabetic proteinuria, Syndrome X and glaucoma.

  本发明涉及一种新型化合物，包括该化合物的组合物，制备该化合物的方法，以及该化合物在治疗中的应用。具体而言，本发明涉及一种在治疗和预防原发性和继发性动脉高血压、中风、心肌缺血、心脏和肾功能不全、心肌梗死、外周血管疾病、糖尿病蛋白尿、X综合征和青光眼中有用的化合物。
• [EN] BIOLUMINESCENT COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSITIONS BIOLUMINESCENTES ET LEURS UTILISATIONS
  申请人：ECOLE POLYTECHNIQUE FED DE LAUSANNE EPFL EPFL DAR TTO

  公开号：WO2021152393A1

  公开（公告）日：2021-08-05

  Compositions and methods for non-invasively monitoring the intracellular processing of a biomolecule are provided. The compositions have a novel thio-luciferin moiety which can be conjugated to the biomolecule directly or via a linker such as disulfide bond wherein the luminescent (such as thio-luciferin) or pro-luminescent (such as thio-cyanobenzothiazoles) moiety is released upon reduction of the disulfide bond upon cytosolic internalization.

  提供了用于非侵入性监测生物分子的细胞内处理的组合物和方法。这些组合物具有一种新颖的硫代鲁西非林基团，可以直接或通过二硫键等连接物与生物分子结合，其中发光基团（如硫代鲁西非林）或前发光基团（如硫代氰基苯并噻唑）在胞浆内摄入后通过还原二硫键释放。
• [EN] COMPOUNDS AND METHODS FOR TRANS-MEMBRANE DELIVERY OF MOLECULES<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR L'ADMINISTRATION TRANSMEMBRANAIRE DE MOLÉCULES
  申请人：APOSENSE LTD

  公开号：WO2019130319A1

  公开（公告）日：2019-07-04

  The Invention provides a novel delivery system for delivery of drugs across biological membranes. It provides novel chemical conjugates that comprise said delivery system, methods for synthesis of said compounds, and methods for utilization of said delivery system, among others, for delivery of genetic drugs into tissues and cells, in vitro, ex vivo, and in vivo, for the treatment of various medical disorders.

  这项发明提供了一种新颖的递送系统，用于跨越生物膜递送药物。它提供了包括该递送系统的新型化学结合物、合成该化合物的方法，以及利用该递送系统的方法等，用于将基因药物递送到组织和细胞中，包括体外、体外和体内，用于治疗各种医学疾病。
• Enzymatic and Organocatalyzed Asymmetric Aldolization Reactions for the Synthesis of Thiosugar Scaffolds
  作者：Johan Fanton、Flora Camps、José A. Castillo、Christine Guérard-Hélaine、Marielle Lemaire、Franck Charmantray、Laurence Hecquet

  DOI：10.1002/ejoc.201101137

  日期：2012.1

  We studied the synthesis of original thiosugar scaffolds by enantioselective aldolization. L-Proline-catalyzed C-C bond formation was the key step in the synthesis of L-erythro-thioketoses (3S,4R), whereas fructose-6-phosphate aldolase-catalyzed reactions yielded the D-threo-thioketose series (3S,4S). By the organocatalytic approach, 5-thio-L-ribulofuranose (1) and 5-deoxy-6-thio-L-psicopyranose (2)

  我们通过对映选择性醛醇化研究了原始硫糖支架的合成。L-脯氨酸催化的 CC 键形成是合成 L-赤型硫酮糖 (3S, 4R) 的关键步骤，而 6-磷酸果糖醛缩酶催化的反应产生 D-苏式硫酮糖系列 (3S, 4S) . 通过有机催化方法，5-硫代-L-呋喃核糖（1）和5-脱氧-6-硫代-L-吡喃吡喃糖（2）以令人满意的总产率从2-卤代乙醛中获得，而5-硫代-D-木酮呋喃糖（ 3) 以 50% 的总产率通过酶促醛醇化反应从相同的起始材料仅两步合成。
• Phase-Transfer Catalyzed Asymmetric [4 + 1] Annulations for the Synthesis of Chiral 2,2-Disubstituted Tetrahydrothiophenes
  作者：Qi Yin、Xiaolu Wen、Yiwei Chen、Xiangnan Gong、Lin Hu

  DOI：10.1021/acs.orglett.1c02744

  日期：2021.10.1

  An efficient catalytic asymmetric [4 + 1] reaction, which features the use of simple β-keto esters as one-carbon nucleophiles and 5-succinimidothio-pent-2-enoates as four-atom bielectrophiles, has been developed in the presence of a bifunctional chiral phase-transfer catalyst. The new annulation provides a distinct protocol to access the functionalized 2-acyl-2-carboxyl tetrahydrothiophenes bearing

  一种高效的催化不对称 [4 + 1] 反应，其特点是使用简单的 β-酮酯作为单碳亲核试剂，使用 5-琥珀酰亚胺硫代-戊-2-烯酸酯作为四原子双亲电试剂，在双功能手性相转移催化剂。新的环化提供了一种独特的协议，以获取具有高非对映选择性和对映选择性的连续季和叔碳立体中心的官能化 2-酰基-2-羧基四氢噻吩。此外，制备的产物可以通过脱苯甲酰化和烷基化反应两个步骤容易地转化为手性 2-烷基-2-羧基四氢噻吩。