7-thia-1,3-diazaspiro[4.4]nonane-2,4-dione | 212710-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 7-thia-1,3-diazaspiro[4.4]nonane-2,4-dione
• 英文别名: 3-thiolanespiro-5'-hydantoin
• CAS: 212710-51-5
• 化学式: C₆H₈N₂O₂S
• mdl: MFCD06363493
• 分子量: 172.208
• InChiKey: MDNCSTBDLRSGIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  7-thia-1,3-diazaspiro[4.4]nonane-2,4-dione 在 barium dihydroxide 、 水 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 methyl 3-acetamidothiolane-3-carboxylate
  参考文献：
  名称：

  A new series of cyclic amino acids as inhibitors of S-adenosyl L-methionine synthetase

  摘要：

  Optically active 3-amino-3-(tetrahydrofuranyl) carboxylic acid, 3-amino-3 -(tetrahydrothienyl) carboxylic acid and their corresponding six membered ring analogues have been synthesised and examined as potential inhibitors of the enzyme S-adenosylmethionine (AdoMet) synthetase.The kinetic behaviour of these compounds was studied using recombinant rat liver AdoMet synthetase (alpha-isoform) fractionated from E. coli transformed with the plasmid pSSRL-T7N. All the compounds tested were competitive inhibitors of the enzyme with respect to L-methionine. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00267-4
• 作为产物：
  描述：

  碳酸氢铵 、 四氢噻吩-3-酮 以 乙醇 、 水 为溶剂， 反应 30.0h， 生成 7-thia-1,3-diazaspiro[4.4]nonane-2,4-dione
  参考文献：
  名称：

  具有3-thiolanespiro-5'-乙内酰脲和4-thio-1 H-四氢吡喃螺-5'-乙内酰脲的新型混合Pt（II）配合物的合成，DFT计算和表征

  摘要：

  顺铂是一种抗癌药物，广泛用于治疗各种实体瘤（头颈部，肺癌，膀胱等），睾丸癌和卵巢癌。由于其严重的毒性和在肿瘤中自发形成耐药性，已合成了许多Pt（II）复合物并测试了其抗肿瘤活性。一些研究集中于使用带有除N以外的供体原子的配体（例如，S，P，O）。两个新的混合的Pt（II）的通式的配合物的顺式- [PT（NH 3）LCL 2 ]其中，L是3- thiolanespiro-5 '乙内酰脲和4-硫基-1- ħ -tetrahydropyranspiro-5 '合成了-hydantom。通过元素分析，熔点，IR和1 H NMR光谱研究了该配合物。混合DFT计算用于优化配体III，IV及其Pt（II）配合物V和VI的结构几何形状。如此计算的结构参数，例如键长和键角，与类似乙内酰脲及其铂络合物的实验数据非常吻合。结果表明，配合物V和VI的几何形状为平面正方形，配体III和IV的边界铂离子受环上硫原子的

  DOI：

  10.1515/chempap-2015-0194

文献信息

• Synthesis, DFT calculations and cytotoxic investigation of platinum complexes with 3-thiolanespiro-5′-hydantoin and 4-thio-1H-tetrahydropyranespiro-5′-hydantoin
  作者：Adriana Bakalova、Rossen Buyukliev、Georgi Momekov

  DOI：10.1016/j.molstruc.2015.02.055

  日期：2015.7

  geometries of the ligand (L1) and its Pt(II) complex (1). The calculated structural parameters such as bond lengths and angles are in good agreement with the experimental data for similar hydantoins and their platinum complexes. The obtained results showed that the geometry of the complex (1) is plane square and the bounding of the L1 with platinum ion is realized by sulfur atom from thiolane ring. The complexes

  摘要 两种有机化合物 - 3-thiolanespiro-5'-hydantoin、4-thio-1H-tetrahydropyranespiro-5'-hydantoin 和四种新的 Pt(II) 和 Pt(IV) 配合物，通式为 cis-[Pt(L)2Cl2 ] 和顺式-[Pt(L)2Cl4] 合成。所得化合物通过元素分析、IR、1H、13C NMR光谱表征。混合 DFT 计算用于优化配体 (L1) 及其 Pt(II) 配合物 (1) 的几何结构。计算的结构参数如键长和角度与类似乙内酰脲及其铂配合物的实验数据非常吻合。所得结果表明配合物(1)的几何形状为平面正方形，L1与铂离子的结合是通过硫烷环中的硫原子实现的。复合物在体外对四种人类肿瘤细胞系的细胞毒性进行了测试。测试的化合物对一些肿瘤细胞系产生浓度依赖性的细胞毒作用。
• Non-covalent interactions reveal the protein chain <i>δ</i> conformation in a flexible single-residue model
  作者：Zeynab Imani、Venkateswara Rao Mundlapati、Valérie Brenner、Eric Gloaguen、Katia Le Barbu-Debus、Anne Zehnacker-Rentien、Sylvie Robin、David J. Aitken、Michel Mons

  DOI：10.1039/d2cc06658k

  日期：——

  structure in proteins that implicates a πamide N–H⋯N interaction between a backbone N atom and the NH of the following residue. Small-molecule models thereof have been limited so far to rigid proline-type compounds. We show here that in derivatives of a cyclic amino acid with a sulphur atom in the γ-position, specific side-chain/backbone N–H⋯S interactions stabilize the δ conformation sufficiently to allow

  δ构象是蛋白质中的局部二级结构，它暗示主链 N 原子和后续残基的 NH 之间的 π酰胺N-H⋯N 相互作用。迄今为止，其小分子模型仅限于刚性脯氨酸型化合物。我们在此表明​​，在 γ 位具有硫原子的环状氨基酸的衍生物中，特定的侧链/主链 N-H⋯S 相互作用足以稳定δ构象，使其能够与经典的 C5 和 C7 H- 竞争保税构象。
• Synthesis of Sterically Hindered <i>N</i>-Acylated Amino Acids from <i>N</i>-Carboxyanhydrides
  作者：Gabriel Schäfer、Jeffrey W. Bode

  DOI：10.1021/ol500523n

  日期：2014.3.7

  Sterically hindered N-acyl, gem-disubstituted amino acids are easily prepared via the addition of organometallic reagents to N-carboxyanhydrides (NCA). The process tolerates a wide variety of functional groups and allows the synthesis of amide products not readily accessible by traditional acylation chemistry. The existence of an isocyanate intermediate was established by in situ IR spectroscopy.
• Synthesis of both enantiomers of cyclic methionine analogue: (R)- and (S)-3-aminotetrahydrothiophene-3-carboxylic acids
  作者：Makoto Oba、Atsushi Shimabukuro、Miyako Ono、Mitsunobu Doi、Masakazu Tanaka

  DOI：10.1016/j.tetasy.2013.03.010

  日期：2013.4

  A method of synthesizing an optically active cyclic methionine analogue, 3-aminotetrahydrothiophene-3-carboxylic acid (At(5)c), is described. A Bucherer-Bergs reaction of 4,5-dihydro-3(2H)-thiophenone and the subsequent alkaline hydrolysis of a hydantoin, followed by Cbz protection of the amine, afforded racemic Cbz-At(5)c (+/-)-3 in excellent yield. Diastereomeric esters derived from Cbz-At(5)c (+/-)-3 and (R)-BINOL could be separated by column chromatography to give both diastereomers with >99% de. X-ray crystallographic analysis revealed the absolute configuration of the synthesized amino acid derived from the less polar diastereomeric ester to be (S). (C) 2013 Elsevier Ltd. All rights reserved.
• [EN] NOVEL DPP1 INHIBITORS AND USES THEREOF<br/>[FR] NOUVEAUX INHIBITEURS DE DPP1 ET LEURS UTILISATIONS
  申请人：[en]INSMED INCORPORATED

  公开号：WO2024026433A2

  公开（公告）日：2024-02-01

  Provided herein are novel DPP1 inhibitor compounds having the general structure of Formula (I), (II) or (III), or a pharmaceutically acceptable salt thereof. Also provided are certain methods of treatment, e.g., a method for treating an obstructive disease of the airway or a method of treating an inflammatory condition with a composition comprising an effective amount of one of the compounds provided herein.