3-[Dimethylsulfamoyl(methyl)amino]-5-methoxycarbonylbenzoic acid | 911789-98-5

• 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: 3-[Dimethylsulfamoyl(methyl)amino]-5-methoxycarbonylbenzoic acid
• CAS: 911789-98-5
• 化学式: C₁₂H₁₆N₂O₆S
• 分子量: 316.335
• InChiKey: LHDVKYIDEKQZBO-UHFFFAOYSA-N

物化性质

• 沸点：
  526.4±50.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[Dimethylsulfamoyl(methyl)amino]-5-methoxycarbonylbenzoic acid 在 sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 二异丙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 1-N-[(2S,3R)-4-(cyclopropylamino)-3-hydroxy-1-phenylbutan-2-yl]-5-[(dimethylsulfamoyl)(methyl)amino]-3-N-[(1R)-1-phenylethyl]benzene-1,3-dicarboxamide
  参考文献：
  名称：

  Structure-Based Design of Potent and Selective Cell-Permeable Inhibitors of Human β-Secretase (BACE-1)

  摘要：

  We describe the development of cell-permeable beta-secretase inhibitors that demonstratively inhibit the production of the secreted amino terminal fragment of an artificial amyloid precursor protein in cell culture. In addition to potent inhibition in a cell-based assay (IC50 < 100 nM), these inhibitors display impressive selectivity against other biologically relevant aspartyl proteases.

  DOI：

  10.1021/jm049379g
• 作为产物：
  描述：

  5-氨基间苯二甲酸二甲酯 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[Dimethylsulfamoyl(methyl)amino]-5-methoxycarbonylbenzoic acid
  参考文献：
  名称：

  Structure-Based Design of Potent and Selective Cell-Permeable Inhibitors of Human β-Secretase (BACE-1)

  摘要：

  We describe the development of cell-permeable beta-secretase inhibitors that demonstratively inhibit the production of the secreted amino terminal fragment of an artificial amyloid precursor protein in cell culture. In addition to potent inhibition in a cell-based assay (IC50 < 100 nM), these inhibitors display impressive selectivity against other biologically relevant aspartyl proteases.

  DOI：

  10.1021/jm049379g

文献信息

• Design, synthesis, and SAR of macrocyclic tertiary carbinamine BACE-1 inhibitors
  作者：Stacey R. Lindsley、Keith P. Moore、Hemaka A. Rajapakse、Harold G. Selnick、Mary Beth Young、Hong Zhu、Sanjeev Munshi、Lawrence Kuo、Georgia B. McGaughey、Dennis Colussi、Ming-Chih Crouthamel、Ming-Tain Lai、Beth Pietrak、Eric A. Price、Sethu Sankaranarayanan、Adam J. Simon、Guy R. Seabrook、Daria J. Hazuda、Nicole T. Pudvah、Jerome H. Hochman、Samuel L. Graham、Joseph P. Vacca、Philippe G. Nantermet

  DOI：10.1016/j.bmcl.2007.04.072

  日期：2007.7

  and synthesis of tertiary carbinamine macrocyclic inhibitors of the beta-secretase (BACE-1) enzyme. These macrocyclic inhibitors, some of which incorporate novel P2 substituents, display a 2- to 100-fold increase in potency relative to the previously described acyclic analogs while affording greater stability.

  这封信描述了β-分泌酶（BACE-1）酶的叔卡宾胺大环抑制剂的设计和合成。这些大环抑制剂，其中一些结合了新的P2取代基，相对于先前描述的无环类似物，其效能提高了2到100倍，同时提供了更高的稳定性。
• COMPOUNDS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
  申请人：Fuchs Klaus

  公开号：US20100144681A1

  公开（公告）日：2010-06-10

  The invention relates to substituted 1,2-ethylenediamines of general formula (I), wherein the radicals R 1 -R 13 , A, B, L and i are as defined in the description and the claims. The invention also relates to the use thereof for treating Alzheimer's disease (AD) and similar diseases.

  该发明涉及一般式(I)的取代1,2-乙二胺化合物，其中基团R1-R13、A、B、L和i如描述和权利要求中所定义。该发明还涉及将其用于治疗阿尔茨海默病（AD）和类似疾病。
• INHIBITORS OF BETA-SECRETASE FOR THE TREATMENT OF ALZHEIMER'S DISEASE
  申请人：Eickmeier Christian

  公开号：US20100298278A1

  公开（公告）日：2010-11-25

  The invention relates to the substituted 1,2-ethylenediamines of general formula (I), wherein the groups R 1 to R 13 , A, B, L and i are defined as in the description and the claims. The invention also relates to the use thereof in the treatment of Alzheimer's disease (AD) and similar diseases.

  该发明涉及通式（I）中的取代1,2-乙二胺化合物，其中基团R1至R13，A，B，L和i的定义如描述和权利要求中所述。该发明还涉及其在治疗阿尔茨海默病（AD）和类似疾病中的用途。
• Substituted 1,2-ethylenediamines, Methods for Preparing Them and Uses Thereof
  申请人：Eickmeier Christian

  公开号：US20090325940A1

  公开（公告）日：2009-12-31

  The present invention relates to substituted 1,2-ethylenediamines of general formula (I) wherein the groups R 1 to R 15 , A, B, L, i as well as X 1 -X 4 are defined as in the specification and claims and the use thereof for the treatment of Alzheimer's disease (AD) and similar diseases.
• SUBSTITUTED 1,2-ETHYLENEDIAMINES, METHODS FOR PREPARING THEM AND USES THEREOF
  申请人：EICKMEIER Christian

  公开号：US20100204160A1

  公开（公告）日：2010-08-12

  The present invention relates to substituted 1,2-ethylenediamines of general formula (I) wherein the groups R 1 to R 15 , A, B, L, i as well as X 1 -X 4 are defined as in the specification and claims and the use thereof for the treatment of Alzheimer's disease (AD) and similar diseases.