N,N-二乙基-4-硼苯磺酰胺 | 850568-76-2

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 磺胺类药及增效剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N-二乙基-4-硼苯磺酰胺
• 中文别名: 4-(N,N-二乙基磺胺苯基)硼酸；4-(二乙基磺酰氨基)苯硼酸
• 英文名称: 4-diethylsulfamoylphenylboronic acid
• 英文别名: N,N-Diethyl 4-boronobenzenesulfonamide；[4-(diethylsulfamoyl)phenyl]boronic acid
• CAS: 850568-76-2
• 化学式: C₁₀H₁₆BNO₄S
• 分子量: 257.118
• InChiKey: HMGSSHUKMMHXLR-UHFFFAOYSA-N

物化性质

• 熔点：
  120-124
• 沸点：
  428.2±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2935009090
• 危险性防范说明：
  P210,P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P370+P378,P403+P233,P403+P235,P405,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (R)-1-[2-(4-bromo-phenyl)-ethyl]-2-methyl-pyrrolidine 、 N,N-二乙基-4-硼苯磺酰胺 在 四(三苯基膦)钯 、 sodium carbonate 、 盐酸 作用下， 以 乙醇 、 水 、 苯 、 甲醇 、 乙醚 为溶剂， 反应 0.5h， 以12%的产率得到4'-[2-((R)-2-methyl-pyrrolidin-1-yl)-ethyl]-biphenyl-4-sulfonic acid diethylamide hydrochloride
  参考文献：
  名称：

  具有强组胺H 3受体反向激动剂活性的新型联苯磺酰胺衍生物的设计与评价

  摘要：

  组胺-H 3受体的拮抗作用是探索增加清醒性以治疗诸如过度日间嗜睡（EDS）以及其他睡眠或认知障碍之类的疾病的一种策略。含有苯乙基-R -2-甲基吡咯烷的联苯磺酰胺化合物被证明是H 3受体的有效和选择性拮抗剂。这些化合物中的几种在（R）-α-甲基组胺（RAMH）诱导的成瘾症的大鼠模型中具有体内活性，一种化合物（4e）通过多导睡眠监测法测量了大鼠的清醒度。但是，对PK / PD关系的更详细分析表明存在共同的活性代谢物，这可能会使该系列化合物无法进一步开发。

  DOI：

  10.1021/jm900857n

文献信息

• SUBSTITUTED NAPHTHYLACETIC ACIDS
  申请人：Hoffmann-La Roche Inc.

  公开号：US20130225588A1

  公开（公告）日：2013-08-29

  The invention is concerned with the compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 and X are defined in the detailed description and claims. In addition, the present invention relates to methods of manufacturing and using the compounds of formula I as well as pharmaceutical compositions containing such compounds. The compounds of formula I are antagonists or partial agonists at the CRTH2 receptor and may be useful in treating diseases and disorders associated with that receptor such as asthma.

  这项发明涉及式(I)的化合物： 及其药学上可接受的盐，其中R 1 ，R 2 ，R 3 和X在详细说明和权利要求中有定义。此外，本发明涉及制造和使用式I的化合物的方法，以及含有这种化合物的药物组合物。式I的化合物是CRTH2受体的拮抗剂或部分激动剂，可能在治疗与该受体相关的疾病和紊乱方面有用，如哮喘。
• Substituted naphthylacetic acids
  申请人：Hoffmann-La Roche Inc.

  公开号：US09000044B2

  公开（公告）日：2015-04-07

  The invention is concerned with the compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein R1, R2, R3 and X are defined in the detailed description and claims. In addition, the present invention relates to methods of manufacturing and using the compounds of formula I as well as pharmaceutical compositions containing such compounds. The compounds of formula I are antagonists or partial agonists at the CRTH2 receptor and may be useful in treating diseases and disorders associated with that receptor such as asthma.

  本发明涉及公式（I）的化合物及其药学上可接受的盐，其中R1、R2、R3和X在详细说明和权利要求中有定义。此外，本发明还涉及制造和使用公式I化合物的方法，以及包含这些化合物的药物组合物。公式I的化合物是CRTH2受体的拮抗剂或部分激动剂，可用于治疗与该受体相关的疾病和障碍，如哮喘。
• Improved Protein Kinase C Affinity through Final Step Diversification of a Simplified Salicylate-Derived Bryostatin Analog Scaffold
  作者：Paul A. Wender、Daryl Staveness

  DOI：10.1021/ol502492b

  日期：2014.10.3

  Bryostatin 1 an clinical trials or preclinical development for cancer, Alzheimer disease, and a first of-its-kind strategy for HIV/AIDS eradication, is neither readily available nor optimally suited for clinical use. In preceding work, we disclosed a new class of simplified bryostatin analogs designed for ease of access and tunable activity. Here we describe a final step diversification strategy that provides in only 25 synthetic steps, simplified and tunable analogs with bryostatin like PKC modulatory activities.
• Inhibition of Chikungunya Virus-Induced Cell Death by Salicylate-Derived Bryostatin Analogues Provides Additional Evidence for a PKC-Independent Pathway
  作者：Daryl Staveness、Rana Abdelnabi、Katherine E. Near、Yu Nakagawa、Johan Neyts、Leen Delang、Pieter Leyssen、Paul A. Wender

  DOI：10.1021/acs.jnatprod.5b01017

  日期：2016.4.22

  Chikungunya virus (CHIKV) has been spreading rapidly, with over one million confirmed or suspected cases in the Americas since late 2013. Infection with CHIKV causes devastating arthritic and arthralgic symptoms. Currently, there is no therapy to treat this disease, and the only medications focus on relief of symptoms. Recently, protein kinase C (PKC) modulators have been reported to inhibit CHIKV-induced cell death in cell assays. The salicylate-derived bryostatin analogues described here are structurally simplified PKC modulators that are more synthetically accessible than the natural product bryostatin 1, a PKC modulator and clinical lead for the treatment of cancer, Alzheimer's disease, and HIV eradication. Evaluation of the anti-CHIKV activity of these salicylate-derived bryostatin analogues in cell culture indicates that they are among the most potent cell-protective agents reported to date. Given that they are more accessible and significantly more active than the parent natural product, they represent new therapeutic leads for controlling CHIKV infection. Significantly, these analogues also provide evidence for the involvement of a PKC-independent pathway. This. adds a fundamentally distinct aspect to the importance or involvement of PKC modulation in inhibition of chikungunya virus replication, a topic of recent and growing interest.