6-benzyloxy-naphthalene-2-sulfonyl chloride, AldrichCPR | 186550-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-benzyloxy-naphthalene-2-sulfonyl chloride, AldrichCPR
• 英文别名: 6-phenylmethoxynaphthalene-2-sulfonyl chloride
• CAS: 186550-79-8
• 化学式: C₁₇H₁₃ClO₃S
• 分子量: 332.807
• InChiKey: BQTHNGZXYBVSFF-UHFFFAOYSA-N

物化性质

• 沸点：
  504.3±30.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-benzyloxy-naphthalene-2-sulfonyl chloride, AldrichCPR 、 D-谷氨酸二甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以372 mg的产率得到(R)-dimethyl 2-(6-(benzyloxy)naphthalene-2-sulfonamido)pentanedioate
  参考文献：
  名称：

  Novel Naphthalene-N-sulfonyl-d-glutamic Acid Derivatives as Inhibitors of MurD, a Key Peptidoglycan Biosynthesis Enzyme,

  摘要：

  Mur ligases have essential roles in the biosynthesis of peptidoglycan, and they represent attractive targets for the design of novel antibacterials. MurD (UDP-N-acetylmuramoyl-L-alanine:D-glutamate ligase) is the second enzyme in the series of Mur ligases, and it catalyzes the addition of D-glutamic acid (D-Glu) to the cytoplasmic intermediate UDP-N-acetylmuramoyl-L-alanine (UMA). Because of the high binding affinity of D-Glu toward MurD, we synthesized and biochemically evaluated a series of N-substituted D-Glu derivatives as potential inhibitors of MurD from E. coli, which allowed us to explore the structure-activity relationships.The substituted naphthalene-N-sulfonyl-D-Glu inhibitors, which were synthesized as potential transition state analogues, displayed IC50 values ranging from 80 to 600 microM. In addition, the high-resolution crystal structures of MurD in complex with four novel inhibitors revealed details of the binding mode of the inhibitors within the active site of MurD. Structure-activity relationships and cocrystal structures constitute an excellent starting point for further development of novel MurD inhibitors of this structural class.

  DOI：

  10.1021/jm800762u
• 作为产物：
  描述：

  sodium 6-(benzyloxy)naphthalene-2-sulfonate 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-benzyloxy-naphthalene-2-sulfonyl chloride, AldrichCPR
  参考文献：
  名称：

  Novel Naphthalene-N-sulfonyl-d-glutamic Acid Derivatives as Inhibitors of MurD, a Key Peptidoglycan Biosynthesis Enzyme,

  摘要：

  Mur ligases have essential roles in the biosynthesis of peptidoglycan, and they represent attractive targets for the design of novel antibacterials. MurD (UDP-N-acetylmuramoyl-L-alanine:D-glutamate ligase) is the second enzyme in the series of Mur ligases, and it catalyzes the addition of D-glutamic acid (D-Glu) to the cytoplasmic intermediate UDP-N-acetylmuramoyl-L-alanine (UMA). Because of the high binding affinity of D-Glu toward MurD, we synthesized and biochemically evaluated a series of N-substituted D-Glu derivatives as potential inhibitors of MurD from E. coli, which allowed us to explore the structure-activity relationships.The substituted naphthalene-N-sulfonyl-D-Glu inhibitors, which were synthesized as potential transition state analogues, displayed IC50 values ranging from 80 to 600 microM. In addition, the high-resolution crystal structures of MurD in complex with four novel inhibitors revealed details of the binding mode of the inhibitors within the active site of MurD. Structure-activity relationships and cocrystal structures constitute an excellent starting point for further development of novel MurD inhibitors of this structural class.

  DOI：

  10.1021/jm800762u

文献信息

• [EN] CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE LA CÉRAMIDE GALACTOSYLTRANSFÉRASE POUR LE TRAITEMENT DE MALADIES
  申请人：BIOMARIN PHARM INC

  公开号：WO2018118838A1

  公开（公告）日：2018-06-28

  Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

  本文描述了化合物、制备这种化合物的方法、含有这种化合物的药物组合物和药物，以及使用这种化合物治疗或预防与酶神经鞘糖脂转移酶（CGT）相关的疾病或紊乱的方法，例如溶酶体贮积症。溶酶体贮积症的例子包括 Krabbe 病和白质变性白血病。
• SUBSTITUTED (SULFINIC ACID, SULFONIC ACID, SULFONYLAMINO OR SULFINYLAMINO) N- (AMINOIMINOMETHYL)PHENYLALKYL -AZAHETEROCYCLYLAMIDE COMPOUNDS
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP0853618B1

  公开（公告）日：2011-08-17
• SUBSTITUTED (SULFINIC ACID, SULFONIC ACID, SULFONYLAMINO OR SULFINYLAMINO) N- (AMINOIMINOMETHYL)PHENYLALKYL]-AZAHETEROCYCLYLAMIDE COMPOUNDS
  申请人：RHONE-POULENC RORER PHARMACEUTICALS, INC.

  公开号：EP0853618A1

  公开（公告）日：1998-07-22
• EP0853618A4
  申请人：——

  公开号：EP0853618A4

  公开（公告）日：2000-03-15
• CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE
  申请人：BioMarin Pharmaceutical Inc.

  公开号：US20190322676A1

  公开（公告）日：2019-10-24

  Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.