4-氨基-1,1-二氧代-四氢-2H-硫代吡喃-4-羧酸 | 39124-27-1

• 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
• 中文名称: 4-氨基-1,1-二氧代-四氢-2H-硫代吡喃-4-羧酸
• 英文名称: 4-amino-4-carboxy-1,1-dioxo-tetrahydrothiopyran
• 英文别名: 4-aminotetrahydro-2H-thiopyran-4-carboxylic acid 1,1-dioxide；4-amino-1,1-dioxothiane-4-carboxylic acid
• CAS: 39124-27-1
• 化学式: C₆H₁₁NO₄S
• mdl: MFCD09607995
• 分子量: 193.224
• InChiKey: FANFYQGRZWKLBT-UHFFFAOYSA-N

物化性质

• 沸点：
  483.5±45.0 °C(Predicted)
• 密度：
  1.471±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (9Ci)-4-[[(1,1-二甲基乙氧基)羰基]氨基]四氢-2H-硫代吡喃-4-羧酸,1,1-二氧化物 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以97%的产率得到4-氨基-1,1-二氧代-四氢-2H-硫代吡喃-4-羧酸
  参考文献：
  名称：

  Inhibition of glutamate racemase by substrate–product analogues

  摘要：

  D-Glutamate is an essential biosynthetic building block of the peptidoglycans that encapsulate the bacterial cell wall. Glutamate racemase catalyzes the reversible formation of D-glutamate from L-glutamate and, hence, the enzyme is a potential therapeutic target. We show that the novel cyclic substrate-product analogue (R,S)-1-hydroxy-1-oxo-4-amino-4-carboxyphosphorinane is a modest, partial noncompetitive inhibitor of glutamate racemase from Fusobacterium nucleatum (FnGR), a pathogen responsible, in part, for periodontal disease and colorectal cancer (K-i = 3.1 +/- 0.6 mM, cf. K-m = 1.41 +/- 0.06 mM). The cyclic substrate- product analogue (R, S)-4-amino-4-carboxy-1,1-dioxotetrahydro-thiopyran was a weak inhibitor, giving only similar to 30% inhibition at a concentration of 40 mM. The related cyclic substrate-product analogue 1,1-dioxo-tetrahydrothiopyran-4-one was a cooperative mixed-type inhibitor of FnGR (K-i = 18.4 +/- 1.2 mM), while linear analogues were only weak inhibitors of the enzyme. For glutamate racemase, mimicking the structure of both enantiomeric substrates (substrate-product analogues) serves as a useful design strategy for developing inhibitors. The new cyclic compounds developed in the present study may serve as potential lead compounds for further development. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.114

文献信息

• [EN] PROTEOGLYCAN MIMETICS FOR ENHANCED WOUND HEALING, ANGIOGENESIS, AND VASCULAR REPAIR<br/>[FR] MIMÉTIQUES DE PROTÉOGLYCANE POUR UNE CICATRISATION, UNE ANGIOGENÈSE ET UNE RÉPARATION VASCULAIRE AMÉLIORÉES
  申请人：UNIV CALIFORNIA

  公开号：WO2019195780A1

  公开（公告）日：2019-10-10

  The present disclosure provides pro-angiogenic proteoglycan mimetics that can provide a provisional, pro-angiogenic scaffold to support tissue regeneration while limiting systemic exposure to VEGF activity. These mimetics can protect a collagen matrix from rapid degradation, and in conjunction with EPCs promote angiogenesis in order to accelerate ischemic wound healing. For example, the provided compounds can be delivered from the end of a catheter following balloon angioplasty to coat the collagen exposed areas, prevent platelet binding and thrombosis, support capture of EPCs from blood to facilitate reendothelialization, and reduce late-lumen loss (neointimal hyperplasia).

  本公开提供了促血管生成的蛋白聚糖类似物，可以提供一个暂时的、促血管生成的支架，支持组织再生，同时限制系统暴露于VEGF活性。这些类似物可以保护胶原基质免受快速降解，并与EPCs一起促进血管生成，以加速缺血性伤口愈合。例如，所提供的化合物可以从导管的末端输送，经过球囊扩张后涂覆暴露的胶原区域，防止血小板结合和血栓形成，支持从血液中捕获EPCs以促进再内皮化，减少晚期腔隙损失（内膜增生）。
• [EN] PEPTIDES FOR ACTIVATION OF CELL SIGNALING IN OSTEOPROGENITOR CELLS<br/>[FR] PEPTIDES POUR L'ACTIVATION DE LA SIGNALISATION CELLULAIRE DANS DES CELLULES OSTÉOPROGÉNITRICES
  申请人：UNIV CALIFORNIA

  公开号：WO2020018941A1

  公开（公告）日：2020-01-23

  The present invention provides compounds and pharmaceutical compositions of peptidomimetic ligands. The peptidomimetic ligands can be conjugated with phosphonate drugs. The compounds and pharmaceutical compositions of the present invention are useful in the treatment of osteoporosis and for the promotion of bone growth due to their specificity for the α4β1 integrin on mesenchymal stem cells and for the surface of bone.

  本发明提供了肽类模拟配体的化合物和制药组合物。这些肽类模拟配体可以与膦酸盐药物结合。本发明的化合物和制药组合物由于其对于骨髓干细胞上的α4β1整合素和骨表面的特异性而可用于治疗骨质疏松症和促进骨生长。
• [EN] LLP2A-BISPHOSPHONATE CONJUGATES FOR OSTEOPOROSIS TREATMENT<br/>[FR] CONJUGUÉS LLP2A-BISPHOSPHONATE POUR LE TRAITEMENT DE L'OSTÉOPOROSE
  申请人：UNIV CALIFORNIA

  公开号：WO2013032527A1

  公开（公告）日：2013-03-07

  The present invention provides compounds and pharmaceutical compositions of a peptidomimetic ligand, e.g. LLP2A, conjugated with a bisphosphonate drug, e.g. Alendronate. The compounds and pharmaceutical compositions of the present invention are useful in the treatment of osteoporosis and for the promotion of bone growth due to their specificity for the α4β1 integrin on mesenchymal stem cells and for the surface of bone.

  本发明提供了一种肽类模拟配体化合物和制药组合物，例如LLP2A，与双磷酸盐药物，例如阿伦膦酸，结合。本发明的化合物和制药组合物由于对间充质干细胞上的α4β1整合素和骨表面的特异性，对骨质疏松症的治疗和促进骨生长具有用处。
• Alpha-4 beta-1 integrin ligands for imaging and therapy
  申请人：Lam S. Kit

  公开号：US20060019900A1

  公开（公告）日：2006-01-26

  The present invention provides α 4 β 1 integrin ligands that display high binding affinity, specificity, and stability. The ligands comprise a peptide having n independently selected amino acids, wherein at least one amino acid is an unnatural amino acid or a D-amino acid, and wherein n is an integer of from 3 to 20. Methods are provided for administering the ligands for treating cancer, inflammatory diseases, and autoimmune diseases. Also provided are methods for administering the ligands for imaging a tumor, organ, or tissue in a subject.

  本发明提供了α4β1整合素配体，该配体具有高结合亲和力、特异性和稳定性。该配体包括具有n个独立选择的氨基酸的肽，其中至少一个氨基酸是非天然氨基酸或D-氨基酸，n为3到20的整数。提供了用于治疗癌症、炎症性疾病和自身免疫疾病的配体给药方法。还提供了用于在受试者中成像肿瘤、器官或组织的配体给药方法。
• LLP2A- BISPHOSPHONATE CONJUGATES FOR OSTEOPOROSIS TREATMENT
  申请人：The Regents of the University of California

  公开号：EP3453711A1

  公开（公告）日：2019-03-13

  The present invention provides compounds and pharmaceutical compositions of a peptidomimetic ligand, e.g. LLP2A, conjugated with a bisphosphonate drug, e.g. Alendronate. The compounds and pharmaceutical compositions of the present invention are useful in the treatment of osteoporosis and for the promotion of bone growth due to their specificity for the α4β1 integrin on mesenchymal stem cells and for the surface of bone.

  本发明提供了拟肽配体（如LLP2A）与双膦酸盐药物（如阿仑膦酸盐）共轭的化合物和药物组合物。由于本发明的化合物和药物组合物对间充质干细胞上的α4β1整合素和骨表面具有特异性，因此可用于治疗骨质疏松症和促进骨生长。