乙酰乙酰对苯磺酰胺 | 4542-32-9

• 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: 乙酰乙酰对苯磺酰胺
• 英文名称: N-[4-(aminosulfonyl)phenyl]-3-oxobutanamide
• 英文别名: 3-oxo-N-(4-sulfamoylphenyl)butanamide；p-Sufamoylacetacetanilid；N-acetoacetyl-sulfanilic acid amide；Acetessigsaeure-(4-sulfamoyl-anilid)；N-[4-(aminosulfonyl)phenyl]-3-oxobutyramide；N-Acetoacetyl-sulfanilsaeure-amid；N-(4-(Aminosulphonyl)phenyl)-3-oxobutyramide
• CAS: 4542-32-9
• 化学式: C₁₀H₁₂N₂O₄S
• 分子量: 256.282
• InChiKey: FDZMNCCKUUOJEX-UHFFFAOYSA-N

物化性质

• 熔点：
  257-258 °C
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  115
• 氢给体数：
  2
• 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：

  乙酰乙酰对苯磺酰胺 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 N-[4-(aminosulfonyl)phenyl]-5-cyano-6-({2-[(4-ethylphenyl)amino]-2-oxoethyl}thio)-4-(2-furyl)-2-methyl-1,4-dihydropyridine-3-carboxamide
  参考文献：
  名称：

  Inhibitors of Tick-Borne Flavivirus Reproduction from Structure-Based Virtual Screening

  摘要：

  Flaviviruses form a large family of enveloped viruses affecting millions of people over the world. To date, no specific therapy was suggested for the infected people, making the treatment exclusively symptomatic. Several attempts were performed earlier for the design of fusion inhibitors for mosquito-borne flaviviruses, whereas for the tick-borne flaviviruses such design had not been performed. We have constructed homology models of envelope glycoproteins of tick-transmitted flaviviruses with the detergent binding pocket in the open state. Molecular docking of substituted 1,4-dihydropyridines and pyrido[2,1-b][1,3,5]-thiadiazines was made against these models, and 89 hits were selected for the in vitro experimental evaluation. Seventeen compounds showed significant inhibition against tick-borne encephalitis virus, Powassan virus, or Omsk hemorrhagic fever virus in the 50% plaque reduction test in PEK. cells. These compounds identified through rational design are the first ones possessing reproduction inhibition activity against tick-borne flaviviruses.

  DOI：

  10.1021/ml400226s
• 作为产物：
  描述：

  双乙烯酮 、 磺胺 在 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 乙酰乙酰对苯磺酰胺
  参考文献：
  名称：

  [EN] COMPOUND HAVING AZO SKELETON STRUCTURE, PIGMENT-DISPERSING AGENT, PIGMENT COMPOSITION, PIGMENT DISPERSION, AND TONER
  [FR] COMPOSÉ POSSÉDANT UNE STRUCTURE DE SQUELETTE AZOÏQUE, AGENT DE DISPERSION DE PIGMENTS, COMPOSITION DE PIGMENTS, DISPERSION DE PIGMENTS ET ENCRE EN POUDRE

  摘要：

  本发明提供了一种化合物，能够改善黄色、洋红色、青色和黑色颜料在不溶于水的溶剂和颜料分散剂中的分散性。本发明还提供了一种具有令人满意的着色力的颜料组合物、颜料分散液和色调剂。本发明涉及一种化合物，其结构中的偶氮骨架结构通过连接基与聚合物部分结合。

  公开号：

  WO2014178435A1

文献信息

• Synthesis of Some More Fluorine Heterocyclic Nitrogen Systems Derived From Sulfa Drugs as Photochemical Probe Agents for Inhibition of Vitiligo Disease-Part I
  作者：Reda M. Abdel-Rahman、Mohammad Saleh I. T. Makki、Wafa A. Bawazir

  DOI：10.1155/2011/586063

  日期：——

  Some more new bioactive fluorine heterocyclic systems containing sulfur and nitrogen as five-membered rings: pyrazoline, imidazole, imidazolopyrimidine, thiazolidinone and 1,2,4-triazole derivatives (3-13) have been synthetically derived from the interaction of sulfa drugs with fluorine aromatic aldehyde and/or hexa fluoroacetic anhydride followed by heterocyclization reactions. Former structures of the targets have been deduced upon the help of elemental and spectral data.. Compounds 7a-f, 10c and 13 could be used as photochemical probe agents for inhibition of Vitiligo diseases, in compare with Nystatin and Nalidixic acid.

  一些含有硫和氮作为五元环的新生物活性氟杂环系统：吡唑啉，咪唑，咪唑嘧啶，噻唑烷酮和1,2,4-三唑衍生物（3-13）已经通过磺胺类药物与氟芳香醛和/或六氟乙酸酐的相互作用后进行杂环化反应合成。在元素和光谱数据的帮助下，目标的前体结构已被推导出。化合物7a-f，10c和13可以用作光化学探针剂，用于抑制白癜风疾病，与制霉菌素和萘啶酸相比。
• Synthesis of <i>β</i> -Ketoamide Curcumin Analogs for Anti-Diabetic and AGEs Inhibitory Activities
  作者：Govindharasu Banuppriya、Rajendran Sribalan、Sulthan Alavudeen Rizwan Fathima、Vediappen Padmini

  DOI：10.1002/cbdv.201800105

  日期：2018.8

  Two different series of novel β-ketoamide curcumin analogs enriched in biological activities have been synthesized. The synthesized compounds were screened for their in vitro anti-diabetic and AGEs inhibitory activities and exhibited potent to good anti-diabetic and AGEs inhibitory activities. The molecular docking study was also performed with the α-amylase enzyme.

  已经合成了两个具有丰富生物活性的不同系列的新型β-酮酰胺姜黄素类似物。筛选合成的化合物的体外抗糖尿病和AGEs抑制活性，并表现出对良好的抗糖尿病和AGEs抑制活性的作用。分子对接研究也使用α-淀粉酶进行。
• Anti‐inflammatory and analgesic effect of LD‐RT and some novel thiadiazole derivatives through COX‐2 inhibition
  作者：Reham M. M. El‐Hazek、Walaa A. El‐Sabbagh、Rania M. El‐Hazek、Marwa G. El‐Gazzar

  DOI：10.1002/ardp.202000094

  日期：2020.10

  highly marketed coxib, so there is still a need for the synthesis of COX‐2 inhibitors with less adverse effects. Moreover, low‐dose radiotherapy (LD‐RT) is clinically used for the treatment of inflammatory diseases. The present study aimed to investigate the analgesic and anti‐inflammatory activity of a novel series of 1,3,4‐thiadiazole derivatives alone or combined with LD‐RT with a single dose of 0

  通常，高选择性 COX-2 抑制剂会引起心血管副作用。塞来昔布是高度上市的昔布，因此仍然需要合成副作用较小的COX-2抑制剂。此外，低剂量放疗（LD-RT）在临床上用于治疗炎症性疾病。本研究旨在研究一系列新型 1,3,4-噻二唑衍生物单独或与单剂量 0.5 Gy LD-RT 联合使用的镇痛和抗炎活性。最初，进行了体外 COX-1/COX-2 抑制试验，确定含磺酰胺的化合物 5-10 是最有效的候选物，IC50 值在 0.32-0.37 µM 范围内，选择性指数最高。在通过急性毒性试验评估其安全性后，对这些化合物和塞来昔布进行了体内试验。用化合物 5-10 治疗将角叉菜胶诱导的水肿抑制了近 47-56%，这几乎与塞来昔布相当。化合物 7、8 和塞来昔布的镇痛活性分别为 64.15%、49.05% 和 84.90%，而化合物 5、6、9 和 10 除非与 LD-RT 联合使用，否则没有任何镇痛
• Synthesis, in vitro Antimicrobial and Anticancer Evaluation of Some New Pyridazines and Polyfunctionally Substituted Heterocyclic Compounds
  作者：F.M.A. Altalbawy

  DOI：10.14233/ajchem.2015.19123

  日期：——

  This study aimed for the synthesis of new heterocyclic compounds incorporating sulfamoyl moiety suitable for use as antimicrobial agents via versatile and readily accessible N-[4-(aminosulfonyl)phenyl]-3-oxobutanamide (1). Butanamide coupled with arenediazonium salts to afford hydrazones. The latter reacts with dimethylformamide dimethyl acetal (DMF-DMA) to afford the substituted 1,4-dihydropyridazine. Several new thiophene, pyridine, nicotinamide and pyrazole derivatives have been synthesized by the reactions of butanamide with malononitrile and elemental sulfur, 1,3-diphenylpropenone, arylidenecyanothioacetamide, nitrogen nucleophiles, respectively. Refluxing of butanamide with a mixture of p-methoxybenzaldehyde and thiourea afforded 4-(4-methoxyphenyl)-6-methyl-N-(4-sulfamoylphenyl)-2-thioxo-1,2-dihydropyrimidine-5-carboxamide which heated with chloroacetyl chloride give N-[4-(aminosulfonyl)phenyl]-7-methyl-5-(4-methoxyphenyl)-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide. Treatment of butanamide with phenyl isothiocyanate afforded the intermediate salt which reacted in situ with 2-bromo-1-phenylethanone to afford N-[4-(aminosulfonyl)phenyl]-2-(3,4-diphenyl-3H-thiazol-2-ylidene)-3-oxobutanamide. Some of the selected products were evaluated for both their in vitro antibacterial and antifungal activities and showed promising results. In addition, the anticancer activity of some selected products against human liver (HEPG2) cell line was determined and the results revealed high activities of compounds 5a, 6 and 14.

  本研究旨在通过用途广泛且易于获得的 N-[4-（氨基磺酰基）苯基]-3-氧代丁酰胺（1），合成含有适合用作抗菌剂的氨基磺酰基的新杂环化合物。丁酰胺与腙盐偶联生成酰肼。后者与二甲基甲酰胺二甲基缩醛（DMF-DMA）反应，生成取代的 1,4-二氢哒嗪。丁酰胺分别与丙二腈和元素硫、1,3-二苯基丙烯酮、亚芳基氰基硫代乙酰胺、氮亲核剂反应，合成了几种新的噻吩、吡啶、烟酰胺和吡唑衍生物。丁酰胺与对甲氧基苯甲醛和硫脲的混合物回流，得到 4-（4-甲氧基苯基）-6-甲基-N-（4-氨基磺酰基苯基）-2-硫酮-1、然后与氯乙酰氯加热，得到 N-[4-(氨基磺酰基)苯基]-7-甲基-5-(4-甲氧基苯基)-3-氧代-2,3-二氢-5H-[1,3]噻唑并[3,2-a]嘧啶-6-甲酰胺。丁酰胺与异硫氰酸苯酯处理后得到中间盐，中间盐与 2-溴-1-苯乙酮原位反应，得到 N-[4-(氨基磺酰基)苯基]-2-(3,4-二苯基-3H-噻唑-2-亚基)-3-氧代丁酰胺。对所选的一些产品进行了体外抗菌和抗真菌活性评估，结果表明这些产品具有良好的抗菌和抗真菌活性。此外，还测定了一些选定产品对人类肝脏（HEPG2）细胞系的抗癌活性，结果表明化合物 5a、6 和 14 具有很高的活性。
• Synthesis of sulfamoyl-triazolyl-carboxamides as pharmacological myeloperoxidase inhibitors
  作者：Allya Larroza、Roberta Krüger、Mariana G. Fronza、Ana Paula Pesarico、Daniela H. de Oliveira、Lucielli Savegnago、Diego Alves

  DOI：10.1039/d2nj01926d

  日期：——

  We describe herein the synthesis, molecular docking, protein–ligand interactions and biological validation of 1,2,3-triazolyl-carboxamides containing sulfonamide moieties as anti-inflammatory agents through the inhibition of myeloid hemoprotein myeloperoxidase (MPO) activity. The named compounds were synthesized in good yields under mild conditions, by a [3+2]-cycloaddition reaction of sulfamoyl-β-oxo-amides

  我们在本文中描述了通过抑制骨髓血红蛋白髓过氧化物酶 (MPO) 活性作为抗炎剂的 1,2,3-三唑基羧酰胺的合成、分子对接、蛋白质-配体相互作用和生物学验证。在催化量的 1,8-二氮杂双环 [5.4.0 ]undec-7-ene (DBU)。鉴于某些合成化合物与 MPO 的较高亲和力，如先前报道的脂多糖，它们对小鼠血浆的抑制活性进行了评估。所得结果表明氨磺酰-1,2,