ND-364 | 869577-61-7

• 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: ND-364
• 英文别名: N-(4-(4-(thiiran-2-ylmethylsulfonyl)phenoxy)phenyl)acetamide；N-[4-[4-(thiiran-2-ylmethylsulfonyl)phenoxy]phenyl]acetamide
• CAS: 869577-61-7
• 化学式: C₁₇H₁₇NO₄S₂
• 分子量: 363.458
• InChiKey: QNKSDDQPRLWOEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(4-(4-((oxiran-2-ylmethyl)sulfonyl)phenoxy)phenyl)acetamide 在 硫脲 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以89.6%的产率得到ND-364
  参考文献：
  名称：

  Synthesis of chiral ND-322, ND-364 and ND-364 derivatives as selective inhibitors of human gelatinase

  摘要：

  Compounds 10 (ND-322) and 15 (ND-364) are potent selective inhibitors for gelatinases, matrix metalloproteinase 2 (MMP2) and matrix metalloproteinase 9 (MMP9). However, both of them are racemates. Herein we report facile synthesis of optically active (R)- and (S)-enantiomers of compounds 10 and 15. And the sulfonyl of 15 was transformed to sulfinyl to obtain four epimeric mixtures. All synthesized thiirane-based compounds were evaluated in MMP2 and MMP9 inhibitory assays. Our results indicated that the configuration of thiirane moiety had little effects on gelatinase inhibition, but the substitution of sulfinyl for sulfonyl was detrimental to gelatinase inhibition. Besides, all target compounds exhibited no inhibition against other two Zn2+ dependant metalloproteases, aminopeptidase N (APN) and histone deacetylases (HDACs), which confirmed the unique Zn2+ chelation mechanism of thiirane moiety against gelatinases. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.013

文献信息

• [EN] ACCELERATION OF DIABETIC WOUND HEALING<br/>[FR] ACCÉLÉRATION DE LA CICATRISATION DES PLAIES DIABÉTIQUES
  申请人：UNIV NOTRE DAME DU LAC

  公开号：WO2016044844A1

  公开（公告）日：2016-03-24

  The invention provides compounds, compositions, and methods to improve or accelerate the healing of a wound. In various embodiments, the methods can include the topical treatment of the wound with the enzyme MMP-8, or the topical treatment of the wound with MMP-8 in combination with administration of an MMP-9 inhibitor, to accelerate the healing of the wound.

  本发明提供了化合物、组成物和方法，以改善或加速伤口的愈合。在各种实施例中，该方法可以包括使用酶MMP-8局部治疗伤口，或者使用MMP-8与MMP-9抑制剂的联合局部治疗伤口，以加速伤口的愈合。
• Inhibitors of Matrix Metallaproteinases
  申请人：Lee Mijoon

  公开号：US20090005420A1

  公开（公告）日：2009-01-01

  The present invention provides novel compounds of formulas I-IX, as described herein. Also provided are compositions of compounds of formulas I-IX, methods of making compounds of formulas I-IX, and methods of using compounds of formulas I-IX. The compounds of the invention can be used to inhibit matrix metalloproteinases, and are useful to treat conditions and diseases associated therewith.

  本发明提供了式I-IX的新化合物，如本文所述。还提供了式I-IX化合物的组合物，制备式I-IX化合物的方法以及使用式I-IX化合物的方法。本发明中的化合物可用于抑制基质金属蛋白酶，并可用于治疗与之相关的疾病和症状。
• INHIBITORS OF MATRIX METALLOPROTEINASES
  申请人：Lee Mijoon

  公开号：US20110224275A1

  公开（公告）日：2011-09-15

  The present invention provides novel compounds of formulas I-IX, as described herein. Also provided are compositions of compounds of formulas I-IX, methods of making compounds of formulas I-IX, and methods of using compounds of formulas I-IX. The compounds of the invention can be used to inhibit matrix metalloproteinases, and are useful to treat conditions and diseases associated therewith.

  本发明提供了如公式I-IX所述的新化合物。还提供了公式I-IX化合物的组合物、制备公式I-IX化合物的方法以及使用公式I-IX化合物的方法。本发明的化合物可用于抑制基质金属蛋白酶，并可用于治疗与之相关的疾病和病症。
• Selective matrix metalloproteinase inhibitors
  申请人：University of Notre Dame du Lac

  公开号：US10253013B2

  公开（公告）日：2019-04-09

  The invention provides compounds, compositions, and methods for the treatment of diseases, disorders, or conditions that are modulated by matrix metalloproteinases (MMPs). The compounds can be selective MMP inhibitors, for example, selective inhibitors of MMP-2, MMP-9, and/or MMP-14. The disease, disorder, or condition can include, for example, stroke, neurological disorders, ophthalmological disorders, or wounds, such as chronic wounds or diabetic wounds.

  本发明提供了用于治疗受基质金属蛋白酶（MMPs）调节的疾病、失调或病症的化合物、组合物和方法。这些化合物可以是选择性 MMP 抑制剂，例如，MMP-2、MMP-9 和/或 MMP-14 的选择性抑制剂。疾病、失调或病症可包括中风、神经失调、眼科失调或伤口，如慢性伤口或糖尿病伤口等。
• Acceleration of diabetic wound healing
  申请人：University of Notre Dame du Lac

  公开号：US10357546B2

  公开（公告）日：2019-07-23

  The invention provides compounds, compositions, and methods to improve or accelerate the healing of a wound. In various embodiments, the methods can include the topical treatment of the wound with the enzyme MMP-8, or the topical treatment of the wound with MMP-8 in combination with administration of an MMP-9 inhibitor, to accelerate the healing of the wound.

  本发明提供了改善或加速伤口愈合的化合物、组合物和方法。在各种实施方案中，这些方法可包括用 MMP-8 酶局部治疗伤口，或用 MMP-8 结合 MMP-9 抑制剂局部治疗伤口，以加速伤口愈合。