Phenyl N-(2,5-xylyl)carbamate | 202599-14-2

• 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: Phenyl N-(2,5-xylyl)carbamate
• 英文别名: phenyl N-(2,5-dimethylphenyl)carbamate
• CAS: 202599-14-2
• 化学式: C₁₅H₁₅NO₂
• mdl: MFCD00089188
• 分子量: 241.29
• InChiKey: QSPJNINDDPSNLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Phenyl N-(2,5-xylyl)carbamate 在 一水合肼 作用下， 反应 12.0h， 生成 N-(2.5-Dimethylphenyl)-semicarbazid
  参考文献：
  名称：

  新型二氢青蒿素衍生物的合成和抗疟活性。

  摘要：

  恶性疟原虫半胱氨酸蛋白酶 falcipain-2 是抗疟药物设计中最有希望的靶点之一，作为血红蛋白降解途径中的主要肽水解酶，在寄生虫存活中起着关键作用。在这项工作中，设计并合成了一系列基于（硫代）缩氨基脲支架的新型双氢青蒿素衍生物作为潜在的 falcipain-2 抑制剂。体外生物测定表明，大多数目标化合物对 P. falciparum falcipain-2 显示出优异的抑制活性，IC(50) 值在 0.29-10.63 μM 范围内。进行分子对接研究以研究抑制剂的结合亲和力和相互作用模式。总结了初步的SARs，可以作为进一步研究抗疟药物开发的基础。

  DOI：

  10.3390/molecules16064527
• 作为产物：
  描述：

  2,5-二甲基苯胺 、 氯甲酸苯酯 在 吡啶 作用下， 反应 2.0h， 生成 Phenyl N-(2,5-xylyl)carbamate
  参考文献：
  名称：

  设计，合成和生物学评估新型半碳水化合物-硒代色氮-4-酮杂化物作为有效的抗真菌剂。

  摘要：

  通过分子杂交的方法，设计合成了一系列新颖的2，3-二氢-4 H -1-苯并硒啉-4-酮（硫代）半碳zone酮衍生物。所有目标化合物均通过HRMS和NMR进行了表征，并针对五种病原菌株评估了其体外抗真菌活性。与前体硒代苯并二氢吡喃-4-酮相比，本研究中的杂化分子显示出显着的抗真菌活性。值得注意的是，化合物B8对除烟曲霉以外的其他菌株均表现出显着的抗真菌活性（白色念珠菌为0.25μg/ mL，新隐球菌为2μg/ mL，玉米芽孢杆菌为8μg / mL）。氟康唑敏感菌株白色念珠菌（Candida albicans）的浓度为2μg/ mL ）。此外，化合物B8，B9和C2还显示出对四种氟康唑耐药菌株的最有效活性。特别地，杂合分子B8对耐氟康唑的菌株的MIC值在0.5-2μg/ mL的范围内。因此，本研究中的分子杂交方法为抗真菌药物的开发提供了新思路。

  DOI：

  10.1016/j.bmcl.2019.126726

文献信息

• Synthesis and Antimalarial Activity of Novel Dihydro-Artemisinin Derivatives
  作者：Yang Liu、Kunqiang Cui、Weiqiang Lu、Wei Luo、Jian Wang、Jin Huang、Chun Guo

  DOI：10.3390/molecules16064527

  日期：——

  The Plasmodium falciparum cysteine protease falcipain-2, one of the most promising targets for antimalarial drug design, plays a key role in parasite survival as a major peptide hydrolase within the hemoglobin degradation pathway. In this work, a series of novel dihydroartemisinin derivatives based on (thio)semicarbazone scaffold were designed and synthesized as potential falcipain-2 inhibitors. The

  恶性疟原虫半胱氨酸蛋白酶 falcipain-2 是抗疟药物设计中最有希望的靶点之一，作为血红蛋白降解途径中的主要肽水解酶，在寄生虫存活中起着关键作用。在这项工作中，设计并合成了一系列基于（硫代）缩氨基脲支架的新型双氢青蒿素衍生物作为潜在的 falcipain-2 抑制剂。体外生物测定表明，大多数目标化合物对 P. falciparum falcipain-2 显示出优异的抑制活性，IC(50) 值在 0.29-10.63 μM 范围内。进行分子对接研究以研究抑制剂的结合亲和力和相互作用模式。总结了初步的SARs，可以作为进一步研究抗疟药物开发的基础。
• Design and synthesis of novel triazole antifungal derivatives by structure-based bioisosterism
  作者：Chunquan Sheng、Xiaoying Che、Wenya Wang、Shengzheng Wang、Yongbing Cao、Zhenyuan Miao、Jianzhong Yao、Wannian Zhang

  DOI：10.1016/j.ejmech.2011.03.019

  日期：2011.11

  The incidence of life-threatening fungal infections is increasing dramatically. In an attempt to develop novel antifungal agents, our previously synthesized phenoxyalkylpiperazine triazole derivatives were used as lead structures for further optimization. By means of structure-based bioisosterism, triazolone was used as a new bioisostere of oxygen atom. This type of bioisosteric replacement can improve the water solubility without loss of hydrogen-bonding interaction with the target enzyme. A series of triazolone-containing triazoles were rationally designed and synthesized. As compared with fluconazole, several compounds showed higher antifungal activity with broader spectrum, suggesting their potential for further evaluations. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis and evaluation in vitro of 1-[2-(10-dihydroartemisininoxy) ethyl]-3-phenylurea derivatives as potential agents against cancer
  作者：Wei Luo、Ming-yu Xia、Takashi Ikejima、Li-hua Li、Chun Guo

  DOI：10.1007/s00044-012-0319-0

  日期：2013.7

  In order to develop potent and selective anticancer agents, a series of novel artemisinin derivatives bearing urea moiety 1a-n were facilely synthesized herein and screened for their activities in vitro against ten human tumor cell lines (HeLa, MCF-7, U937, K562, HL60, HCT116, HepG2, A549, A375-S2, and HT1080). The pharmacological results indicated that some compounds showed excellent activity against cancer cell lines and good selectivity, especially the compound 1c which proved to be the most active against the cancer cells as well as distinctive patterns of selectivity.
• Structure‐guided design of potent JAK1‐selective inhibitors based on 4‐amino‐7<i>H</i>‐pyrrolo[2,3‐<i>d</i>]pyrimidine with anti‐inflammatory efficacy
  作者：Jiahao Zhang、Shuming Xing、Jianming Cui、Xiujian Wei、Zhi Cao、Bin Shao、Nan Jiang、Xin Zhai

  DOI：10.1002/ardp.202300591

  日期：2024.4

  In a continuous effort to develop Janus kinase 1 (JAK1)‐selective inhibitors, a novel series of 4‐amino‐7H‐pyrrolo[2,3‐d]pyrimidine derivatives bearing the piperidinyl fragment were designed and synthesized according to a combination strategy. Through enzymatic assessments, the superior compound 12a with an IC₅₀ value of 12.6 nM against JAK1 was identified and a 10.7‐fold selectivity index over JAK2 was achieved. It was indicated that 12a displayed considerable effect in inhibiting the pro‐inflammatory NO generated from lipopolysaccharide (LPS)‐induced RAW264.7 macrophages, while on normal RAW264.7 cells, 12a exerted a weak cytotoxicity effect (IC₅₀ = 143.3 μM). Furthermore, H&E stain assay demonstrated the conspicuous capacity of 12a to suppress CCl₄‐induced hepatic fibrosis levels in a dose‐dependent manner in vivo. The binding model of 12a ideally reflects the excellent activity of JAK1 over the homologous kinase JAK2. Overall, 12a, a JAK1‐selective inhibitor, exhibited potential for liver fibrosis and inflammatory diseases.
• Design, synthesis and biological evaluation of novel semicarbazone-selenochroman-4-ones hybrids as potent antifungal agents
  作者：Hang Xu、Xin Su、Xiao-qian Liu、Kai-peng Zhang、Zhuang Hou、Chun Guo

  DOI：10.1016/j.bmcl.2019.126726

  日期：2019.12

  A series of novel 2,3-dihydro-4H-1-benzoselenin-4-one (thio)semicarbazone derivatives were designed and synthesized by using molecular hybridization approach. All the target compounds were characterized by HRMS and NMR and evaluated in vitro antifungal activity angainst five pathogenic strains. In comparison with precursor selenochroman-4-ones, the hybrid molecules in this study showed significant

  通过分子杂交的方法，设计合成了一系列新颖的2，3-二氢-4 H -1-苯并硒啉-4-酮（硫代）半碳zone酮衍生物。所有目标化合物均通过HRMS和NMR进行了表征，并针对五种病原菌株评估了其体外抗真菌活性。与前体硒代苯并二氢吡喃-4-酮相比，本研究中的杂化分子显示出显着的抗真菌活性。值得注意的是，化合物B8对除烟曲霉以外的其他菌株均表现出显着的抗真菌活性（白色念珠菌为0.25μg/ mL，新隐球菌为2μg/ mL，玉米芽孢杆菌为8μg / mL）。氟康唑敏感菌株白色念珠菌（Candida albicans）的浓度为2μg/ mL ）。此外，化合物B8，B9和C2还显示出对四种氟康唑耐药菌株的最有效活性。特别地，杂合分子B8对耐氟康唑的菌株的MIC值在0.5-2μg/ mL的范围内。因此，本研究中的分子杂交方法为抗真菌药物的开发提供了新思路。