N-[4-(aminosulfonylphenyl)]-3-pyridinecarboxamide | 41538-37-8

• 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: N-[4-(aminosulfonylphenyl)]-3-pyridinecarboxamide
• 英文别名: 4-(nicotinoylamido)-benzenesulfonamide；N-(4-sulfamoylphenyl)nicotinamide；nicotinic acid-(4-sulfamoyl-anilide)；Nicotinsaeure-(4-sulfamoyl-anilid)；N-(4-sulfamoylphenyl)pyridine-3-carboxamide
• CAS: 41538-37-8
• 化学式: C₁₂H₁₁N₃O₃S
• 分子量: 277.304
• InChiKey: CWUUKGVTFGECDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  烟酰氯 、 N-[4-(aminosulfonylphenyl)]-3-pyridinecarboxamide 在 吡啶 作用下， 生成 nicotinoyl-(N-nicotinoyl-sulfanilyl)-amine
  参考文献：
  名称：

  N¹,N⁴-Nicotinyl Derivatives of Sulfanilamide

  摘要：

  DOI：

  10.1021/ja01861a013
• 作为产物：
  描述：

  烟酰苯胺 在 氯磺酸 作用下， 生成 N-[4-(aminosulfonylphenyl)]-3-pyridinecarboxamide
  参考文献：
  名称：

  N¹,N⁴-Nicotinyl Derivatives of Sulfanilamide

  摘要：

  DOI：

  10.1021/ja01861a013

文献信息

• A New Application of Parallel Synthesis Strategy for Discovery of Amide-Linked Small Molecules as Potent Chondroprotective Agents in TNF-α-Stimulated Chondrocytes
  作者：Chia-Chung Lee、Yang Lo、Ling-Jun Ho、Jenn-Haung Lai、Shiu-Bii Lien、Leou-Chyr Lin、Chun-Liang Chen、Tsung-Chih Chen、Feng-Cheng Liu、Hsu-Shan Huang

  DOI：10.1371/journal.pone.0149317

  日期：——

  Among the tested compounds, N-(3-chloro-4-fluorophenyl)-2-hydroxybenzamide (HS-Ck) was the most potent inhibitor of NO production and inducible nitric oxide synthase (iNOS) expression in TNF-α-stimulated chondrocytes. In addition, our biological results indicated that HS-Ck might suppress the expression levels of iNOS and matrix metalloproteinases-13 (MMP-13) activities through downregulating the activation

  作为剖析潜在的治疗炎症相关疾病的方法的一部分，使用并行合成策略合成了多种酰胺连接的小分子。此外，还通过使用肿瘤坏死因子α（TNF-α）诱导的软骨细胞炎症反应评估了这些新化合物对一氧化氮（NO）的抑制作用。在测试的化合物中，N-（3-氯-4-氟苯基）-2-羟基苯甲酰胺（HS-Ck）是TNF-α刺激的软骨细胞中NO产生和诱导型一氧化氮合酶（iNOS）表达最有效的抑制剂。此外，我们的生物学结果表明，HS-Ck可能通过下调核因子κB（NF-κB）的激活以及信号转导和转录激活因子3（STAT）的表达而抑制iNOS和基质金属蛋白酶-13（MMP-13）的表达水平。 -3）转录因子。因此，平行合成成功地用于开发一类新的潜在抗炎药，作为治疗骨关节炎的软骨保护候选物。
• Van Es, Theodorus; Staskun, Benjamin; Karuso, Peter, South African Journal of Chemistry, 2012, vol. 65, p. 53 - 61
  作者：Van Es, Theodorus、Staskun, Benjamin、Karuso, Peter

  DOI：——

  日期：——
• Carbonic anhydrase inhibitors – part 70. Synthesis and ocular pharmacology of a new class of water-soluble, topically effective intraocular pressure lowering agents derived from nicotinic acid and aromatic/heterocyclic sulfonamides
  作者：C Supuran

  DOI：10.1016/s0223-5234(99)00212-3

  日期：1999.10

  Reaction of twenty atomatic/heterocyclic sulfonamides containing a free amino, imino, hydrazino or hydroxyl group, with nicotinoyl chloride afforded a series of water-soluble (as hydrochloride or triflate salts) compounds. The new derivatives were assayed as inhibitors of three carbonic anhydrase (CA) isozymes, hCA I, hCA II (cytosolic forms) and bCA IV (membrane-bound form); h = human, b = bovine isozyme. Efficient inhibition was observed against all three isozymes, but especially against hCA II and bCA IV (in nanomolar range), two isozymes known to play a critical role in aqueous humour secretion within the ciliary processes of the eye. Some of the best inhibitors synthesized were applied as 2% water solutions directly into the eye of normotensive or glaucomatous albino rabbits. Very strong intraocular pressure (IOP) lowering was observed for many of them, and the active drug was detected in eye tissues and fluids. This result prompted us to re-analyse the synthetic work done by other groups for the design of water soluble, topically effective antiglaucoma sulfonamides. According to these researchers, the IOP lowering effect is due to the intrinsic nature of the specific heterocyclic sulfonamide considered, among which the thienothiopyran-2-sulfonamide derivatives represent the best studied case. Indeed, the first agents developed for such applications, such as dorzolamide, are derivatives of this ring system. In order to prove that the tail (in this case the nicotinoyl moiety) conferring water solubility to a sulfonamide CA inhibitor is critically important, similarly to the ring to which the sulfonamido group is grafted, we also prepared a dorzolamide derivative to which the nicotinoyl moiety was attached. This new compound is more water soluble than dorzolamide (as hydrochloride salt), behaves as a strong CA II inhibitor, and acts similarly to the parent derivative in lowering IOP in experimental animals. Thus, it seems that the tail conferring water solubility is more important for topical activity as an antiglaucoma drug than the heterocyclic/aromatic ring to which the sulfonamido moiety is grafted. (C) 1999 Editions scientifiques et medicales Elsevier SAS.
• ARYLTHIO COMPOUNDS AS ANTIBACTERIAL AND ANTIVIRAL AGENTS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0775110A1

  公开（公告）日：1997-05-28
• [EN] ARYLTHIO COMPOUNDS AS ANTIBACTERIAL AND ANTIVIRAL AGENTS<br/>[FR] COMPOSES ARYLTHIO UTILISES COMME AGENTS ANTIBACTERIENS ET ANTIVIRAUX
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1996004242A1

  公开（公告）日：1996-02-15

  (EN) Arylthiol and dithiobisarylamide antibacterial and antiviral agents have general formula (I) where A is monocyclic or bicyclic aryl which can contain up to 3 heteroatoms selected from O, S, and N, R1 and R2 are substituent groups, X is (a), (b), (c), or SO2NR4Z, Y is H or SZ when n is 1, a single bond when n is 2; R4 and Z can be hydrogen or alkyl.(FR) L'invention concerne des agents antibactériens et antiviraux à base d'arylthiol et de dithiobisarylamide représentés par la formule générale (I). Dans cette formule, A est un aryle monocyclique ou bicyclique qui peut renfermer jusqu'à 3 hétéroatomes choisis parmi O, S et N; R1 et R2 sont des groupes substituants; X est un groupe (a), (b), (c) ou SO2NR4Z; Y représente H ou SZ lorsque n est égal à 1, une liaison simple lorsque n est égal à 2; R4 et Z peuvent représenter chacun hydrogène ou alkyle.