2-(cyclopropylamino)-5-methoxybenzenesulfonamide | 1204575-07-4

• 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: 2-(cyclopropylamino)-5-methoxybenzenesulfonamide
• 英文别名: 2-Cyclopropylamino-5-methoxybenzenesulphonamide
• CAS: 1204575-07-4
• 化学式: C₁₀H₁₄N₂O₃S
• 分子量: 242.299
• InChiKey: DZNOYXBHTHLOAV-UHFFFAOYSA-N

物化性质

• 沸点：
  470.1±55.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(cyclopropylamino)-5-methoxybenzenesulfonamide 在 吡啶 、 sodium tetrahydroborate 、 copper diacetate 、 三溴化硼 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 31.17h， 生成 4-cyclopropyl-7-(3-hydroxyphenoxy)-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxide
  参考文献：
  名称：

  Radiosynthesis of a carbon-11-labeled AMPAR allosteric modulator as a new PET radioligand candidate for imaging of Alzheimer’s disease

  摘要：

  To develop PET tracers for imaging of Alzheimer's disease, a new carbon-11-labeled AMPAR allosteric modulator 4-cyclopropyl-7-(3-[C-11] methoxyphenoxy)-3,4-dihydro-2H-benzo[e][1,2,4] thiadiazine 1,1-dioxide ([C-11] 8) has been synthesized. The reference standard 4-cyclopropyl-7-(3-methoxyphenoxy)-3,4-dihydro-2H-benzo[e][1,2,4] thiadiazine 1,1-dioxide (8) and its corresponding desmethylated precursor 4-cyclopropyl-7-(3-hydroxyphenoxy)3,4- dihydro-2H-benzo[e][1,2,4] thiadiazine 1,1-dioxide (9) were synthesized from 4-methoxyabiline and chlorosulfonyl isocyanate in eight and nine steps with 3% and 1% overall chemical yield, respectively. The target tracer [C-11] 8 was prepared from the precursor 9 with [C-11] CH3OTf through O-[C-11] methylation and isolated by HPLC combined with SPE in 10-15% radiochemical yield, based on [C-11] CO2 and decay corrected to end of bombardment (EOB). The radiochemical purity was> 99%, and the molar activity (AM) at EOB was 370-740 GBq/mu mol with a total synthesis time of 35-40-minutes from EOB.

  DOI：

  10.1016/j.bmcl.2019.03.027
• 作为产物：
  描述：

  2-氨基-5-甲氧基-苯磺酰胺 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 34.0h， 生成 2-(cyclopropylamino)-5-methoxybenzenesulfonamide
  参考文献：
  名称：

  Radiosynthesis of a carbon-11-labeled AMPAR allosteric modulator as a new PET radioligand candidate for imaging of Alzheimer’s disease

  摘要：

  To develop PET tracers for imaging of Alzheimer's disease, a new carbon-11-labeled AMPAR allosteric modulator 4-cyclopropyl-7-(3-[C-11] methoxyphenoxy)-3,4-dihydro-2H-benzo[e][1,2,4] thiadiazine 1,1-dioxide ([C-11] 8) has been synthesized. The reference standard 4-cyclopropyl-7-(3-methoxyphenoxy)-3,4-dihydro-2H-benzo[e][1,2,4] thiadiazine 1,1-dioxide (8) and its corresponding desmethylated precursor 4-cyclopropyl-7-(3-hydroxyphenoxy)3,4- dihydro-2H-benzo[e][1,2,4] thiadiazine 1,1-dioxide (9) were synthesized from 4-methoxyabiline and chlorosulfonyl isocyanate in eight and nine steps with 3% and 1% overall chemical yield, respectively. The target tracer [C-11] 8 was prepared from the precursor 9 with [C-11] CH3OTf through O-[C-11] methylation and isolated by HPLC combined with SPE in 10-15% radiochemical yield, based on [C-11] CO2 and decay corrected to end of bombardment (EOB). The radiochemical purity was> 99%, and the molar activity (AM) at EOB was 370-740 GBq/mu mol with a total synthesis time of 35-40-minutes from EOB.

  DOI：

  10.1016/j.bmcl.2019.03.027

文献信息

• Cycloalkylated benzothiadiazines, a process for their preparation and pharmaceutical compostions containing them
  申请人：FRANCOTTE Pierre

  公开号：US20100009974A1

  公开（公告）日：2010-01-14

  Compounds of formula (I): wherein: R Cy represents an unsubstituted or substituted cycloalkyl group or cycloalkylalkyl group, R 1 , R 2 , R 3 and R 4 , which may be the same or different, each represent a hydrogen or halogen atom or a nitro group; a cyano group; a hydroxy group; an alkoxy group; an alkyl group; an unsubstituted or substituted amino group; a carboxy group; an alkoxycarbonyl group; an aryloxycarbonyl group; an unsubstituted or substituted aminocarbonyl group. Medicinal products containing the same which are useful in treating or preventing conditions treatable by an AMPA receptor modulator.

  式（I）的化合物：其中：RCy表示未取代或取代的环烷基或环烷基烷基，R1、R2、R3和R4，可以相同也可以不同，每个代表氢或卤素原子或硝基团；氰基；羟基；烷氧基；烷基；未取代或取代的氨基团；羧基；烷氧羰基；芳基氧羰基；未取代或取代的氨基羰基。含有这些化合物的药物产品，可用于治疗或预防通过AMPA受体调节剂可治疗的疾病。
• Enthalpy-Entropy Compensation in the Binding of Modulators at Ionotropic Glutamate Receptor GluA2
  作者：Christian Krintel、Pierre Francotte、Darryl S. Pickering、Lina Juknaitė、Jacob Pøhlsgaard、Lars Olsen、Karla Frydenvang、Eric Goffin、Bernard Pirotte、Jette S. Kastrup

  DOI：10.1016/j.bpj.2016.04.032

  日期：2016.6

  earlier compounds was the orientation of Ser-497 pointing toward the hydroxyl group of 5. The favorable enthalpy can be explained by the formation of a hydrogen bond from the side-chain hydroxyl group of Ser-497 to the hydroxyl group of 5, whereas the unfavorable entropy might be due to desolvation effects combined with a conformational restriction of Ser-497 and 5. In summary, this study shows a remarkable

  离子型谷氨酸受体 A2 (GluA2) 的 1,2,4-苯并噻二嗪 1,1-二氧化物类型的正变构调节剂是治疗认知障碍（例如阿尔茨海默病）的有前景的先导化合物。调节剂在由两个相邻配体结合域的界面形成的裂缝中结合，并通过稳定激动剂结合的开放通道构象而起作用。这些调节剂结合背后的驱动力可以显着改变，只需对母体分子进行少量替换。在这项研究中，我们表明将调节剂 BPAM97 (2) 和 BPAM344 (3) 的 7-氟取代基改变为羟基（分别为 BPAM557 (4) 和 BPAM521 (5)），会导致更有利的结合焓。 ΔH，kcal/mol) 从 -4.9 (2) 和 -7.5 (3) 到 -6.2 (4) 和 -14.5 (5)，但也有一个不太有利的结合熵 (-TΔS, kcal/mol)，从 -2.3 (2) 和 -1.3 (3) 到 -0.5 (4) 和 4.8 (5)。因此，4 (11.2)
• Cycloalkylated benzothiadiazines, a process for their preparation and pharmaceutical compositions containing them
  申请人：Les Laboratoires Servier

  公开号：US07741320B2

  公开（公告）日：2010-06-22

  Compounds of formula (I): wherein: RCy represents an unsubstituted or substituted cycloalkyl group or cycloalkylalkyl group, R1, R2, R3 and R4, which may be the same or different, each represent a hydrogen or halogen atom or a nitro group; a cyano group; a hydroxy group; an alkoxy group; an alkyl group; an unsubstituted or substituted amino group; a carboxy group; an alkoxycarbonyl group; an aryloxycarbonyl group; an unsubstituted or substituted aminocarbonyl group. Medicinal products containing the same which are useful in treating or preventing conditions treatable by an AMPA receptor modulator.

  化合物的公式（I）： 其中： RCy代表未取代或取代的环烷基或环烷基烷基， R1、R2、R3和R4可以相同也可以不同，分别代表氢原子或卤素原子或硝基基团；氰基；羟基；烷氧基；烷基；未取代或取代的氨基基团；羧基；烷氧羰基基团；芳基氧羰基基团；未取代或取代的氨基羰基基团。 含有上述化合物的药物可用于治疗或预防可通过AMPA受体调节剂治疗的疾病。
• Nouveaux dérivés de benzothiadiazines cycloalkylées, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：Les Laboratoires Servier

  公开号：EP2147915B1

  公开（公告）日：2010-09-15
• US7741320B2
  申请人：——

  公开号：US7741320B2

  公开（公告）日：2010-06-22