N-(4-(N-acetylsulfamoyl)phenyl)-2-chloroacetamide | 97433-27-7

• 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-(N-acetylsulfamoyl)phenyl)-2-chloroacetamide
• 英文别名: Chlor-essigsaeure-(4-acetamidosulfonyl-anilid)；N-[4-(acetylsulfamoyl)phenyl]-2-chloroacetamide
• CAS: 97433-27-7
• 化学式: C₁₀H₁₁ClN₂O₄S
• mdl: MFCD01343603
• 分子量: 290.727
• InChiKey: DVYZZCCUUTXKAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 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：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-(N-acetylsulfamoyl)phenyl)-2-chloroacetamide 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 N-{[4-((5-((1H-indol-3-yl)methylene)-4-oxo-4,5-dihydrothiazol-2-yl)amino)phenyl]sulfonyl}acetamide
  参考文献：
  名称：

  Inhibition studies on a panel of human carbonic anhydrases withN1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails

  摘要：

  Being the primary sulfonamide among the most efficient zinc binding group (ZBG) to design inhibitors for the metallo-enzymes carbonic anhydrases (CA, EC 4.2.1.1), herein, we propose an investigation on four physiologically important human (h) CAs (hCA I, II, IV, and IX) with N-1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails. The effect of the functionalisation of the sulfonamide group with five different substitution patterns, namely acetyl, pyridine, thiazole, pyrimidine, and carbamimidoyl, was evaluated in relation to the inhibition profile of the corresponding primary sulfonamide analogues. With most of these latter being nanomolar inhibitors of all four considered isoforms, a totally counterproductive effect on the inhibition potency can be ascribed to N-1-functionalisations of the ZBG primary sulfonamide structure with pyridine, thiazole, and pyrimidine moieties. On the other hand, incorporation of less hindered groups, such as sulfonylacetamides and sulfonylguanidines, maintained a certain degree of activity dependent on the tailing moiety, with K(I)s spanning in the low micromolar range.

  DOI：

  10.1080/14756366.2018.1446432
• 作为产物：
  描述：

  氯乙酰氯 、 磺胺醋酰 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-(4-(N-acetylsulfamoyl)phenyl)-2-chloroacetamide
  参考文献：
  名称：

  作为潜在 VEGFR-2 抑制剂的新型喹唑啉-4(3H)-酮的设计、合成和抗增殖评估

  摘要：

  抑制 VEGFR-2 已被确立为治疗癌症的治疗策略。因此，设计并合成了19 种新的喹唑啉-4(3 H )-one 衍生物。使用 MTT 分析方法对合成的化合物对三种人类癌细胞系（HepG-2、MCF-7 和 HCT-116）的初步细胞毒性研究进行了评估。多柔比星和索拉非尼用作阳性对照。发现五种化合物对所有细胞系都具有良好的细胞毒活性。化合物16 f含有一个 2-氯-5-硝基苯基，已成为最活跃的成员。它对 HepG2、HCT-116 和 MCF-7 细胞的活性分别比阿霉素高约 4.39、5.73 和 1.96 倍，比索拉非尼高 3.88、5.59 和 1.84 倍。最活跃的细胞毒性剂在体外进一步评估了它们的 VEGFR-2 抑制活性。体外VEGFR-2 抑制的结果与细胞毒性数据的结果一致。此外，这些化合物与激酶结构域的分子对接支持了结果。

  DOI：

  10.1016/j.bmc.2020.115872

文献信息

• Design, molecular docking, in vitro, and in vivo studies of new quinazolin-4(3H)-ones as VEGFR-2 inhibitors with potential activity against hepatocellular carcinoma
  作者：Ibrahim.H. Eissa、Mohammed K. Ibrahim、Ahmed M. Metwaly、Amany Belal、Ahmed B.M. Mehany、Alsayed A. Abdelhady、Mostafa A. Elhendawy、Mohamed M. Radwan、Mahmoud A. ElSohly、Hazem A. Mahdy

  DOI：10.1016/j.bioorg.2020.104532

  日期：2021.2

  synthesized and evaluated for their anti-proliferative activities against hepatocellular carcinoma (HepG-2 cell line). Compound 29b (IC50 = 4.33 ± 0.2 µg/ml) was found to be the most potent derivative as it has showed to be more active than doxorubicin (IC50 = 4.50 ± 0.2 µg/ml) and 78% of sorafenib activity (IC50 = 3.40 ± 0.25 µg/ml). The inhibitory profiles against VEGFR-2 were also assessed for the most

  设计、合成了一系列新的 VEGFR-2 抑制剂，并评估了它们对肝细胞癌（HepG-2 细胞系）的抗增殖活性。发现化合物29 b (IC 50 = 4.33 ± 0.2 µg/ml) 是最有效的衍生物，因为它已显示出比阿霉素 (IC 50 = 4.50 ± 0.2 µg/ml)更具活性和索拉非尼活性的 78% ( IC 50 = 3.40 ± 0.25 µg/ml)。还评估了最有希望的候选物（16 b、20 c、22 b、24 a、24 b、28 c ）的VEGFR-2 抑制谱。，28 E， 29一，29 b和29 Ç）。与索拉非尼 (IC 50 = 2.4 ± 0.05 µM)相比，化合物29 b、29 c和29 a在 IC 50值分别为 3.1 ± 0.04、3.4 ± 0.05 和 3.7 ± 0.06 µM 时表现出对 VEGFR-2 的有效抑制活性。Furthermorer，化合物29
• Design, Synthesis and Biological Evaluation of Some Novel Chalcones-sulphonamide Hybrids
  作者：Khanusiya, Mahammadali、Gadhawala, Zakirhusen

  DOI：10.5012/jkcs.2018.62.5.377

  日期：——

  A new class of Chalcone-Sulphonamide hybrids has been designed by condensing appropriate sulphonamide scaffold with substituted chalcones tethered by chloroacetyl chloride as a multi-target drug for therapeutic treatment. Chalcones were prepared by Claisen-Schmidt condensation of a substituted aldehyde with para aminoacetophenone. These Chalcone-Sulphonamide hybrids were screened by means of their antibacterial activity by NCCLS method. Among all these compounds, 5e and 5c displayed more potent growth inhibitory activity against Staphylococcus epidermidis and Pseudomonas aeruginosa bacteria respectively. Further, these hybrids were evaluated for their antifungal activity, among all hybrid 5a exhibited potent antifungal activity. The synthesized compounds were characterized by FT-IR, $^1HNMR$, $^13}CNMR$ and HR-LCMS and spectral study supports the structures of synthesized Chalcone-Sulphonamide hybrids.

  通过将适当的磺酰胺支架与氯乙酰氯拴住的取代查耳酮缩合，设计出了一类新的查耳酮-磺酰胺杂交化合物，作为多靶点治疗药物。查耳酮是通过取代醛与对氨基苯乙酮的克莱森-施密特缩合反应制备的。通过 NCCLS 方法对这些查耳酮-磺酰胺杂化物的抗菌活性进行了筛选。在所有这些化合物中，5e 和 5c 分别对表皮葡萄球菌和绿脓杆菌具有更强的生长抑制活性。此外，还对这些杂交化合物的抗真菌活性进行了评估，其中杂交化合物 5a 具有很强的抗真菌活性。通过傅立叶变换红外光谱（FT-IR）、$^1HNMR$、$^13}CNMR$和 HR-LCMS，对合成的化合物进行了表征。
• Synthesis of Some New Benzisothiazolone and Benzenesulfonamide Derivatives of Biological Interest Starting from Saccharin Sodium
  作者：Osama I. El-Sabbagh

  DOI：10.1002/ardp.201300110

  日期：2013.10

  Two new series of benzenesulfonamide (4a–f, 5a–b, 6, 7) and 1,2‐benzisothiazol‐3(2H)‐one‐1,1‐dioxide (9a–c, 10, 12a–d) derivatives were prepared starting from saccharin sodium. The novel compounds were characterized using elemental analyses and different spectroscopic methods. Assessment of the antiviral activities of these novel compounds against a broad panel of viruses in different cell cultures

  两个新系列的苯磺酰胺 (4a-f, 5a-b, 6, 7) 和 1,2-苯并异噻唑-3(2H)-one-1,1-二氧化物 (9a-c, 10, 12a-d) 衍生物是以糖精钠为原料制备。使用元素分析和不同的光谱方法对新化合物进行了表征。对这些新型化合物在不同细胞培养物中对大量病毒的抗病毒活性的评估表明，只有属于苯并异噻唑-3(2H)-one-1,1-二氧化物系列的噻唑衍生物才是活性化合物。所有噻唑衍生物 12a-d 在人胚胎肺 (HEL) 细胞培养中均显示出抗水痘-带状疱疹病毒，尤其是 TK-VZV 毒株 07-1 和巨细胞病毒毒株 AD-169 和 Davis 的活性。
• Selective carbonic anhydrase IX and XII inhibitors based around a functionalized coumarin scaffold
  作者：Bader I. Huwaimel、Sravan K. Jonnalagadda、Shirisha Jonnalagadda、Shikha Kumari、Alessio Nocentini、Claudiu T. Supuran、Paul C. Trippier

  DOI：10.1002/ddr.22049

  日期：——

  potent and selective CA inhibitors. Selected compounds show significant activity and selectivity over CA I and CA II to target the tumor-associated CA IX and CA XII with high inhibition activity at the single digit nanomolar level. Twelve compounds were identified to be more potent compared with acetazolamide (AAZ) control to inhibit CA IX while one was also more potent than AAZ to inhibit CA XII. Compound

  抑制特定碳酸酐酶 (CA) 是开发癌症靶向药物的有效策略。 CA亚型IX和XII在各种人类实体瘤中过度表达，其中它们在调节细胞外肿瘤酸化、增殖和进展中发挥关键作用。设计、合成了一系列基于香豆素支架的新型磺胺类药物，并作为有效的选择性 CA 抑制剂进行表征。所选化合物显示出比 CA I 和 CA II 显着的活性和选择性，可靶向肿瘤相关的 CA IX 和 CA XII，并在个位数纳摩尔水平上具有高抑制活性。与乙酰唑胺 (AAZ) 对照相比，12 种化合物被鉴定为更有效地抑制 CA IX，同时其中一种化合物也比 AAZ 更有效地抑制 CA XII。化合物18f （CA 的 I、II、IX 和 XII 的 Ki 值分别为 955 nM、515 nM、21 nM 和 5 nM）被强调为一种新型 CA IX 和 XII 抑制剂，有待进一步开发。
• Fuerst,H. et al., Journal fur praktische Chemie (Leipzig 1954), 1962, vol. 17, p. 299 - 313
  作者：Fuerst,H. et al.

  DOI：——

  日期：——