N-苄基-3-硼苯磺酰胺 | 690662-91-0

• 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-苄基-3-硼苯磺酰胺
• 英文名称: (3-(N-benzylsulfamoyl)phenyl)boronic acid
• 英文别名: 3-benzylsulfamoylbenzeneboronic acid；N-Benzyl 3-boronobenzenesulfonamide；[3-(benzylsulfamoyl)phenyl]boronic acid
• CAS: 690662-91-0
• 化学式: C₁₃H₁₄BNO₄S
• 分子量: 291.135
• InChiKey: AYVLQZPFDWDKFW-UHFFFAOYSA-N

物化性质

• 熔点：
  194-196℃

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  95
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  N-苄基-3-硼苯磺酰胺 、 6-chloro-3-(4-(methylsulfonyl)phenyl)imidazo[1,2-b]-pyridazine 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3-(3-(4-(methylsulfonyl)phenyl)imidazo[1,2-b]pyridazin-6-yl)benzenesulfonamide
  参考文献：
  名称：

  Medicinal Chemistry Optimization of Antiplasmodial Imidazopyridazine Hits from High Throughput Screening of a SoftFocus Kinase Library: Part 1

  摘要：

  A novel class of imidazopyridazines identified from whole cell screening of a SoftFocus kinase library was synthesized and evaluated for antiplasmodial activity against K1 (multidrug resistant strain) and NF54 (sensitive strain). Structure-activity relationship studies led to the identification of highly potent compounds against both strains. Compound 35 was highly active (IC50: K1 = 6.3 nM, NF54 = 7.3 nM) and comparable in potency to artesunate, and 35 exhibited 98% activity in the in vivo P. berghei mouse model (4-day test by Peters) at 4 × 50 mg/kg po. Compound 35 was also assessed against P. falciparum in the in vivo SCID mouse model where the efficacy was found to be more consistent with the in vitro activity. Furthermore, 35 displayed high (78%) rat oral bioavailability with good oral exposure and plasma half-life. Mice exposure at the same dose was 10-fold lower than in rat, suggesting lower oral absorption and/or higher metabolic clearance in mice.

  DOI：

  10.1021/jm500098s
• 作为产物：
  描述：

  在 sodium hydroxide 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 N-苄基-3-硼苯磺酰胺
  参考文献：
  名称：

  Halo sulfonyl aryl boronates

  摘要：

  本发明涉及一般式（I）的卤磺酰基芳基硼酸酯： 其中Arylene表示一个含有1-3个环的碳环或杂环芳香环系统； R1、R2和R3分别为氢、C1-6烷基、C1-6烷氧基、卤素、硝基、氰基或苯基； X为氟、氯或溴；以及 Y是通过一条键连接到Arylene上的硼氧杂环基，该环具有一个式为Arylene(R1)(R2)(R3)SO2X的基团，在硼氧杂环的另外两个硼原子上，或Y是硼酸基团或硼酯基团。 该发明还涉及一般式（I）化合物的制备以及它们在有机合成中的应用。

  公开号：

  US20040116701A1

文献信息

• [EN] HALO SULFONYL ARYL BORONATES<br/>[FR] HALO SULFONYL ARYL BORONATES
  申请人：NOVO NORDISK AS

  公开号：WO2004041833A1

  公开（公告）日：2004-05-21

  The present invention relates to halo sulfonyl aryl boronates of the general formula (I): wherein Arylene designates a carbocyclic or heterocyclic, aromatic ring system comprising 1-3 rings; R1, R2 and R3 are, independently, hydrogen, C1-6alkyl, C1-6alkoxy, halogen, nitro, cyano or phenyl;X is fluoro, chloro or bromo; and Y is a boroxine moiety attached via a bond from Arylene to one of the boron atoms of a boroxine ring which ring has a group of the formula -Arylene(R1)(R2)(R3)SO2X, wherein Arylene, R1, R2, R3 and X are as defined above, at each of the other two boron atoms of the boroxine ring, or Y is a boronic acid group or a boronic ester group.The invention also relates to the preparation of the compounds of formula (I) and to their use in organic synthesis.

  本发明涉及一般式(I)的卤磺酰基芳基硼酸酯，其中芳烃代表一个包含1-3个环的碳环或杂环芳香环系统；R1、R2和R3分别是氢、C1-6烷基、C1-6烷氧基、卤素、硝基、氰基或苯基；X是氟、氯或溴；Y是通过一种键连接到芳烃上的硼氧杂环部分，该硼氧杂环具有一个式为-Arylene(R1)(R2)(R3)SO2X的基团，其中Arylene、R1、R2、R3和X如上定义，在硼氧杂环的另外两个硼原子上，或Y是硼酸基团或硼酯基团。该发明还涉及一般式(I)化合物的制备以及它们在有机合成中的应用。
• SUBSTITUTED FUROPYRIDINES FOR THERAPEUTIC USE
  申请人：Masarykova Univerzita

  公开号：EP4353727A1

  公开（公告）日：2024-04-17

  The invention relates to furopyridine compounds of formula I: for use in the treatment of FLT3-related, DDR-related and MAP4K-related diseases.

  本发明涉及具有式I结构式的环状吡啶衍生物，用于治疗FLT3相关性疾病、DDR相关性疾病和MAP4K相关性疾病。
• Structure–activity relationship for aryl and heteroaryl boronic acid inhibitors of hormone-sensitive lipase
  作者：Søren Ebdrup、Poul Jacobsen、Anupma Dhanda Farrington、Per Vedsø

  DOI：10.1016/j.bmc.2004.12.042

  日期：2005.3

  A range of aryl and heteroaryl boronic acids were tested for their in vitro hormone-sensitive lipase inhibitory properties. (2-Benzyloxy-5-fluorophenyl)boronic acid, (2-benzyloxy-5-chlorophenyl)boronic acid and 5-bromothiophene-2-boronic acid were found to be the most potent HSL inhibitors with IC50 values of 140, 17 and 350 nm, respectively. (c) 2004 Elsevier Ltd. All rights reserved.
• Halo sulfonyl aryl boronates
  申请人：——

  公开号：US20040116701A1

  公开（公告）日：2004-06-17

  The present invention relates to halo sulfonyl aryl boronates of the general formula (I): 1 wherein Arylene designates a carbocyclic or heterocyclic, aromatic ring system comprising 1-3 rings; R 1 , R 2 and R 3 are, independently, hydrogen, C 1-6 alkyl, C 1-6 alkoxy, halogen, nitro, cyano or phenyl; X is fluoro, chloro or bromo; and Y is a boroxine moiety attached via a bond from Arylene to one of the boron atoms of a boroxine ring which ring has a group of the formula—Arylene(R 1 )(R 2 )(R 3 )SO 2 X, wherein Arylene, R 1 , R 2 , R 3 and X are as defined above, at each of the other two boron atoms of the boroxine ring, or Y is a boronic acid group or a boronic ester group. The invention also relates to the preparation of the compounds of formula (I) and to their use in organic synthesis.

  本发明涉及一般式（I）的卤磺酰基芳基硼酸酯： 其中Arylene表示一个含有1-3个环的碳环或杂环芳香环系统； R1、R2和R3分别为氢、C1-6烷基、C1-6烷氧基、卤素、硝基、氰基或苯基； X为氟、氯或溴；以及 Y是通过一条键连接到Arylene上的硼氧杂环基，该环具有一个式为Arylene(R1)(R2)(R3)SO2X的基团，在硼氧杂环的另外两个硼原子上，或Y是硼酸基团或硼酯基团。 该发明还涉及一般式（I）化合物的制备以及它们在有机合成中的应用。
• Medicinal Chemistry Optimization of Antiplasmodial Imidazopyridazine Hits from High Throughput Screening of a SoftFocus Kinase Library: Part 1
  作者：Claire Le Manach、Diego Gonzàlez Cabrera、Frederic Douelle、Aloysius T. Nchinda、Yassir Younis、Dale Taylor、Lubbe Wiesner、Karen L. White、Eileen Ryan、Corinne March、Sandra Duffy、Vicky M. Avery、David Waterson、Michael J. Witty、Sergio Wittlin、Susan A. Charman、Leslie J. Street、Kelly Chibale

  DOI：10.1021/jm500098s

  日期：2014.3.27

  A novel class of imidazopyridazines identified from whole cell screening of a SoftFocus kinase library was synthesized and evaluated for antiplasmodial activity against K1 (multidrug resistant strain) and NF54 (sensitive strain). Structure-activity relationship studies led to the identification of highly potent compounds against both strains. Compound 35 was highly active (IC50: K1 = 6.3 nM, NF54 = 7.3 nM) and comparable in potency to artesunate, and 35 exhibited 98% activity in the in vivo P. berghei mouse model (4-day test by Peters) at 4 × 50 mg/kg po. Compound 35 was also assessed against P. falciparum in the in vivo SCID mouse model where the efficacy was found to be more consistent with the in vitro activity. Furthermore, 35 displayed high (78%) rat oral bioavailability with good oral exposure and plasma half-life. Mice exposure at the same dose was 10-fold lower than in rat, suggesting lower oral absorption and/or higher metabolic clearance in mice.