3-氨基磺酰基-4-甲氧基苯甲酸 | 20532-06-3

• 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: 3-氨基磺酰基-4-甲氧基苯甲酸
• 英文名称: 4-methoxy-3-(aminosulfonyl)benzoic acid
• 英文别名: 4-methoxy-3-sulfamoylbenzoic acid；2-Methoxy-5-carboxy-benzolsulfonsaeureamid；5-carboxy-2-methoxybenzenesulfonamide；4-Methoxy-3-sulfamoyl-benzoesaeure
• CAS: 20532-06-3
• 化学式: C₈H₉NO₅S
• mdl: MFCD06355949
• 分子量: 231.229
• InChiKey: CKCJWLSXMXMIQO-UHFFFAOYSA-N

物化性质

• 沸点：
  493.8±55.0 °C(Predicted)
• 密度：
  1.492±0.06 g/cm3(Predicted)
• 溶解度：
  >34.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  3-氨基磺酰基-4-甲氧基苯甲酸 在 manganese(IV) oxide 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 21.0h， 生成 5-甲酰基-2-甲氧基-苯磺酰胺
  参考文献：
  名称：

  Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 2. Structure-activity relationships at the phenethylamine binding site

  摘要：

  1-Aralkylimidazole-2-thiones have been shown to be potent multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1). In the present study, a series of 1-benzylimidazole-2-thiones was prepared to explore the effects of substitution in the benzyl ring on the inhibition of DBH. A detailed structure-activity relationship for in vitro activity was discovered and this was shown by a modified Hansch analysis to correlate (r = 0.91) with four key structural features of the benzyl ring: the presence of a hydroxyl at the 4-position, molar refractivity at the 3-, 4-, and 5-positions, inductive effects of the substituents at the 3-, 4-, and 5-positions, and pi-electron density. The affinity (Kis) of eight substituted inhibitors for DBH was shown to correlate (r = 0.75) with the affinity (KD) of comparably substituted tyramines for the ternary DBH-oxygen-tyramine complex. This correlate is used to support the hypothesis that binding of inhibitor to DBH occurs in a fashion that mimics the binding of tyramine substrates. The most potent inhibitors were selected for study in vivo in the spontaneously hypertensive rat model of hypertension. The changes in vascular dopamine and norepinephrine levels that resulted from oral administration of the inhibitors corresponded to the observed reduction in mean arterial blood pressure. A divergence between in vitro potency and in vivo efficacy upon oral dosing was noted and is suggested to result from an in vivo metabolic conjugation of the phenolic group of inhibitor.

  DOI：

  10.1021/jm00386a008
• 作为产物：
  描述：

  3-氯磺酰基-4-甲氧基苯甲酰氯 在 氨 、 水 作用下， 生成 3-氨基磺酰基-4-甲氧基苯甲酸
  参考文献：
  名称：

  321.硫醇衍生自ø - ，米- ，和p -甲氧基甲苯和苯甲酸

  摘要：

  DOI：

  10.1039/jr9330001375

文献信息

• Design and synthesis of benzenesulfonamide‐linked imidazo[2,1‐ <i>b</i> ][1,3,4]thiadiazole derivatives as carbonic anhydrase I and II inhibitors
  作者：Baijayantimala Swain、Kamtam Aashritha、Priti Singh、Andrea Angeli、Abhay Kothari、Dilep K. Sigalapalli、Venkata M. Yaddanapudi、Claudiu T. Supuran、Mohammed Arifuddin

  DOI：10.1002/ardp.202100028

  日期：2021.7

  A novel series of imidazothiadiazole-linked benzenesulfonamide derivatives (5a–t) was synthesized and subjected for screening against the four physiologically and pharmacologically relevant human carbonic anhydrase (hCA) isoforms: hCA I, II, VA, and IX. The compounds selectively inhibited hCA I and II over hCA VA and IX. Furthermore, among the two cytosolic isoforms, hCA II was more effectively inhibited

  合成了一系列新型咪唑并噻二唑连接的苯磺酰胺衍生物 ( 5a – t )，并针对四种生理学和药理学相关的人碳酸酐酶 (hCA) 亚型：hCA I、II、VA 和 IX 进行筛选。与 hCA VA 和 IX 相比，这些化合物选择性抑制 hCA I 和 II。此外，在两种胞质亚型中，与 hCA I 相比，hCA II 受到更有效的抑制。对 hCA II 最活性的化合物是5o （ K i = 0.246 µM）和5p （ K i = 0.376 µM），而化合物5f显示出良好的抑制作用针对 hCA I 和 II， K i分别为 0.493 和 0.4 µM。这类尚未充分研究的磺胺类药物可用于设计针对药物化学感兴趣的酶的异构体选择性 CA 抑制剂。
• [EN] HETEROCYCLIC CHROMENE-SPIROCYCLIC PIPERIDINE AMIDES AS MODULATORS OF ION CHANNELS<br/>[FR] AMIDES DE CHROMÈNE HÉTÉROCYCLIQUE-PIPÉRIDINE SPIROCYCLIQUE UTILES COMME MODULATEURS DES CANAUX IONIQUES
  申请人：VERTEX PHARMA

  公开号：WO2011140425A1

  公开（公告）日：2011-11-10

  The invention relates to heterocyclic chromene-spirocyclic piperidine amides useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及杂环色烯-螺环哌啶酰胺，用作离子通道的抑制剂。本发明还提供了包含本发明化合物的药用可接受组合物，以及使用这些组合物治疗各种疾病的方法。
• [EN] BENZOXAZINES AS MODULATORS OF ION CHANNELS<br/>[FR] BENZOXAZINES COMME MODULATEURS DES CANAUX IONIQUES
  申请人：VERTEX PHARMA

  公开号：WO2013067248A1

  公开（公告）日：2013-05-10

  The invention relates to benzoxazines useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及可用作离子通道抑制剂的苯并噁嗪。本发明还提供了包含本发明化合物的药用可接受组合物，以及使用这些组合物治疗各种疾病的方法。
• Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors
  作者：Baijayantimala Swain、Andrea Angeli、Srinivas Angapelly、Pavitra S. Thacker、Priti Singh、Claudiu T. Supuran、Mohammed Arifuddin

  DOI：10.1080/14756366.2019.1629432

  日期：2019.1.1

  Abstract The synthesis of a novel series of 3-functionalised benzenesulfonamides incorporating phenyl-1,2,3-triazole with an amide linker was achieved by using the “click-tail” approach. The new compounds, including the intermediates, were assayed as inhibitors of human carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and II (cytosolic isoforms) and also for hCA IV and IX (transmembrane isoforms)

  抽象的 通过使用“点击尾巴”方法，可以合成一系列新的3-官能化的苯磺酰胺，这些苯基磺酰胺结合了苯基-1,2,3-三唑和一个酰胺连接基。以乙酰唑醇为标准药物，测定了包括中间体在内的新化合物作为人类碳酸酐酶（CA，EC 4.2.1.1）同工型hCA I和II（胞质同工型）的抑制剂，以及hCA IV和IX（跨膜同工型）的抑制剂。这些化合物中的大多数对所有这些同工型均表现出优异的活性。hCA I被K i s抑制在50.8–966.8 nM的范围内，而青光眼相关的hCA II被K i s抑制在6.5–760.0 nM的范围内。K i抑制同工型hCA IVs的范围为65.3–957.5 nM，而与肿瘤相关的缺氧诱导的hCA IX被K i s抑制的范围为30.8–815.9 nM。从结果还推断出3-官能化的-1-苯基-1,2,3-三唑氨磺酰基苯甲酰胺对抗这些同工型的结构活性关系。
• 3-Functionalised benzenesulphonamide based 1,3,4-oxadiazoles as selective carbonic anhydrase XIII inhibitors: Design, synthesis and biological evaluation
  作者：Baijayantimala Swain、Abhay、Priti Singh、Andrea Angeli、Kamtam Aashritha、Narayana Nagesh、Claudiu T. Supuran、Mohammed Arifuddin

  DOI：10.1016/j.bmcl.2021.127856

  日期：2021.4

  A new series of benzenesulphonamide linked-1,3,4-oxadiazole hybrids (6a–s) has been synthesized and tested for their carbonic anhydrase inhibition against human (h) carbonic anhydrase (CA) isoforms hCA I, II, IX, and XIII. Fluorescence properties of some of the synthesized molecules were studied. Most of the molecules exhibited significant inhibitory power, comparable or better than the standard drug

  合成了一系列新的苯磺酰胺连接的 1,3,4-恶二唑杂化物 ( 6a – s )，并测试了其对人 (h) 碳酸酐酶 (CA) 亚型 hCA I、II、IX 和 XIII 的碳酸酐酶抑制作用。研究了一些合成分子的荧光特性。大多数分子对 hCA XIII 表现出显着的抑制能力，与标准药物乙酰唑胺 (AAZ) 相当或更好。在 19 个测试分子中，化合物6e (75.8 nM) 的抗 hCA I 效力是 AAZ (250.0 nM) 的 3 倍，而化合物6e (15.4 nM)、 6g (16.2 nM)、 6h (16.4 nM) 和6i (17.0 nM) nM) 被发现比 AAZ (17.0 nM) 对抗异构体 hCA XIII 更有效。预计这些化合物可作为开发具有改进效力的选择性 hCA XIII 亚型抑制剂的潜在先导化合物。