2-bromo-2'-ethyl-6'-methylpropionanilide | 53984-87-5

• 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: 2-bromo-2'-ethyl-6'-methylpropionanilide
• 英文别名: 2-bromo-N-(2-ethyl-6-methylphenyl)propanamide
• CAS: 53984-87-5
• 化学式: C₁₂H₁₆BrNO
• 分子量: 270.169
• InChiKey: SQBYZLSKEHLGCY-UHFFFAOYSA-N

物化性质

• 沸点：
  362.3±37.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-2'-ethyl-6'-methylpropionanilide 、 氨 以70%的产率得到
  参考文献：
  名称：

  BYRNES E. W.; MCMASTER P. D.; SMITH E. R.; BLAIR M. R.; BOYES R. N.; DUCE+, J. MED. CHEM., 1979, 22, NO 10, 1171-1176

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-6-乙基苯胺 生成 2-bromo-2'-ethyl-6'-methylpropionanilide
  参考文献：
  名称：

  BYRNES E. W.; MCMASTER P. D.; SMITH E. R.; BLAIR M. R.; BOYES R. N.; DUCE+, J. MED. CHEM., 1979, 22, NO 10, 1171-1176

  摘要：

  DOI：

文献信息

• Microwave‐assisted synthesis of triazole derivatives conjugated with piperidine as new anti‐enzymatic agents
  作者：Naeem A. Virk、Aziz‐ur‐ Rehman、Muhammad A. Abbasi、Sabahat Z. Siddiqui、Javed Iqbal、Shahid Rasool、Shafi U. Khan、Thet T. Htar、Hira Khalid、Sabina J. Laulloo、Syed A. Ali Shah

  DOI：10.1002/jhet.3875

  日期：2020.3

  cyclized into 1,2,4‐triazole (5) nucleus. A series of propanamides, 8a‐r, were synthesized from different amines, 6a‐r. These electrophiles, 8a‐r, were reacted with compound 5 under conventional and microwave‐assisted protocols to acquire the library of hybrids, 9a‐r. The structural confirmations were availed by 1H‐NMR, 13C‐NMR, and IR techniques. The whole series was evaluated for biological potential against

  当前的研究旨在研究基于哌啶的三唑化合物对各种酶的生物学潜力。通过连续步骤（包括形成磺酰胺，酰肼，1,2,4-三唑和硫醚），合成了具有哌啶，1,2,4-三唑和丙酰胺的新型化合物9a-r。最初，使用4-甲氧基苯磺酰氯（1）和异二十二碳六烯酸乙酯（2）来开发1-（4-甲氧基苯基磺酰基）-4-哌啶甲酸乙酯（3）。产物3分别转化为酰肼（4），然后进一步环化成1,2,4-三唑（5）核。一系列的丙酰胺，8a-r是由不同的胺6a-r合成的。这些亲电子体8a-r在常规和微波辅助方案下与化合物5反应，获得了杂合体9a-r库。通过1 H-NMR，13获得结构确认C-NMR和IR技术。评估了整个系列针对乙酰胆碱酯酶（AChE）和α-葡萄糖苷酶的生物潜力。根据合成化合物的结构变化，对不同化合物进行生物学评估的潜力范围从低到高。除少数几种酶外，几乎所有化合物都对两种酶保持活性。牛血清白蛋白（BSA）结合研究证明了药物
• Comparative conventional and microwave assisted synthesis of heterocyclic oxadiazole analogues having enzymatic inhibition potential
  作者：Jamila Javid、Aziz‐ur‐Rehman、Muhammad A. Abbasi、Sabahat Z. Siddiqui、Javed Iqbal、Naeem A. Virk、Shahid Rasool、Hira A. Ali、Muhammad Ashraf、Wardah Shahid、Safdar Hussain、Syed A. Ali Shah

  DOI：10.1002/jhet.4150

  日期：2021.1

  A comparative microwave assisted and conventional synthetic strategies were applied to synthesize heterocyclic 1,3,4‐oxadiazole analogues as active anti‐enzymatic agents. Green synthesis of compound 1 was achieved by stirring 4‐methoxybenzenesulfonyl chloride (a) and ethyl piperidine‐4‐carboxylate (b). Compound 1 was converted into respective hydrazide (2) by hydrazine and then into 1,3,4‐oxadiazole

  比较了微波辅助和常规合成策略，以合成杂环1,3,4-恶二唑类似物作为活性抗酶剂。通过搅拌4-甲氧基苯磺酰氯（a）和哌啶-4-羧酸乙酯（b）实现化合物1的绿色合成。化合物1通过肼分别转化为酰肼（2），然后在回流下通过CS 2转化为1,3,4-恶二唑（3）。合成了亲电子试剂N-烷基/芳烷基/芳基-2-溴丙酰胺（6a-p）并转化为N-烷基/芳烷基/芳基-2-丙酰胺衍生物（7a–p）通过在绿色化学反应下与3反应。发现微波辅助方法相对于常规方法是有效的。利用13 C-NMR，1 H-NMR和IR技术证实了合成化合物的结构，然后针对脂氧合酶（LOX），α-葡萄糖苷酶，乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）酶进行了筛选。许多化合物针对这些酶表现出更好的潜力。针对LOX和α-葡萄糖苷酶的活性最强的化合物进行了分子对接研究，以探索它们与酶活性位点的相互作用。
• Primary aminoacylanilides
  申请人：Astra Pharmaceutical Products, Inc.

  公开号：US04237068A1

  公开（公告）日：1980-12-02

  Primary amino acylanilides of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, methyl, ethyl and propyl, R.sub.2 is selected from the group consisting of methyl, ethyl, chlorine, methoxy and ethoxy, R.sub.3 is selected from the group consisting of hydrogen and methyl, R.sub.4 is selected from the group consisting of hydrogen, methyl, and a C.sub.1 -C.sub.4 alkoxy group, R.sub.6 is selected from the group consisting of methyl, ethyl, chlorine, methoxy and ethoxy, R.sub.7 is hydrogen, methyl or ethyl, R.sub.8 is hydrogen, R.sub.9 is hydrogen, methyl or ethyl, R.sub.10 is hydrogen, and n is 0 or 1, with the provisions that (a) when n is 0, R.sub.8 can also be methyl; (b) when n is 1, and R.sub.7 is hydrogen, and R.sub.9 is hydrogen or methyl, then R.sub.10 can also be methyl; (c) when R.sub.1 is hydrogen, R.sub.2 is methyl, R.sub.3 is hydrogen, R.sub.6 is methyl, R.sub.7 is hydrogen, R.sub.8 is hydrogen, and n is 0, then R.sub.4 can be ethoxy or propoxy only; (d) when R.sub.1 is hydrogen, R.sub.2 is methyl, R.sub.3, R.sub.4, R.sub.7 and R.sub.8 are hydrogen, and n is 0, then R.sub.6 is methoxy, ethoxy, or ethyl only; and the therapeutically acceptable salts thereof. Compounds of this type have been found to be effective longlasting cardiac antiarrhythmic agents, especially when administered by the oral route.

  式子为##STR1##的一级氨基苯甲酰胺，其中R.sub.1选自氢、甲基、乙基和丙基组成的群体，R.sub.2选自甲基、乙基、氯、甲氧基和乙氧基组成的群体，R.sub.3选自氢和甲基组成的群体，R.sub.4选自氢、甲基和C.sub.1-C.sub.4烷氧基组成的群体，R.sub.6选自甲基、乙基、氯、甲氧基和乙氧基组成的群体，R.sub.7为氢、甲基或乙基，R.sub.8为氢，R.sub.9为氢、甲基或乙基，R.sub.10为氢，n为0或1，条件是（a）当n为0时，R.sub.8也可以是甲基；（b）当n为1，且R.sub.7为氢，R.sub.9为氢或甲基时，R.sub.10也可以是甲基；（c）当R.sub.1为氢，R.sub.2为甲基，R.sub.3为氢，R.sub.6为甲基，R.sub.7为氢，R.sub.8为氢，n为0时，R.sub.4只能是乙氧基或丙氧基；（d）当R.sub.1为氢，R.sub.2为甲基，R.sub.3、R.sub.4、R.sub.7和R.sub.8为氢，n为0时，R.sub.6只能是甲氧基、乙氧基或乙基；以及其治疗上可接受的盐。已发现此类化合物在口服时可以成为有效的长效心脏抗心律失常药物。
• Primary aminoacylanilides, methods of making the same and use as
  申请人：Astra Pharmaceutical Products, Inc.

  公开号：US04218477A1

  公开（公告）日：1980-08-19

  Primary amino acylanilides of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, methyl, ethyl and propyl, R.sub.2 is selected from the group consisting of methyl, ethyl, chlorine, methoxy and ethoxy, R.sub.3 is selected from the group consisting of hydrogen and methyl, R.sub.4 is selected from the group consisting of hydrogen, methyl, and a C.sub.1 -C.sub.4 alkoxy group, R.sub.6 is selected from the group consisting of methyl, ethyl, chlorine, methoxy and ethoxy, R.sub.7 is hydrogen, methyl or ethyl, R.sub.8 is hydrogen, R.sub.9 is hydrogen, methyl or ethyl, R.sub.10 is hydrogen, and n is 0 or 1, with the provisions that (a) when n is 0, R.sub.8 can also be methyl; (b) when n is 1, and R.sub.7 is hydrogen, and R.sub.9 is hydrogen or methyl, then R.sub.10 can also be methyl; (c) when R.sub.1 is hydrogen, R.sub.2 is methyl, R.sub.3 is hydrogen, R.sub.6 is methyl, R.sub.7 is hydrogen, R.sub.8 is hydrogen, and n is 0, then R.sub.4 can be ethoxy or propoxy only; (d) when R.sub.1 is hydrogen, R.sub.2 is methyl, R.sub.3, R.sub.4, R.sub.7 and R.sub.8 are hydrogen, and n is 0, then R.sub.6 is methoxy, ethoxy, or ethyl only; and the therapeutically acceptable salts thereof. Compounds of this type have been found to be effective longlasting cardiac antiarrhythmic agents, especially when administered by the oral route.

  式子为##STR1##其中R.sub.1选自氢、甲基、乙基和丙基的群组，R.sub.2选自甲基、乙基、氯、甲氧基和乙氧基的群组，R.sub.3选自氢和甲基的群组，R.sub.4选自氢、甲基和C.sub.1-C.sub.4烷氧基的群组，R.sub.6选自甲基、乙基、氯、甲氧基和乙氧基的群组，R.sub.7为氢、甲基或乙基，R.sub.8为氢，R.sub.9为氢、甲基或乙基，R.sub.10为氢，n为0或1，条件是(a)当n为0时，R.sub.8也可以是甲基；(b)当n为1时，且R.sub.7为氢，R.sub.9为氢或甲基时，R.sub.10也可以是甲基；(c)当R.sub.1为氢，R.sub.2为甲基，R.sub.3为氢，R.sub.6为甲基，R.sub.7为氢，R.sub.8为氢，n为0时，R.sub.4只能是乙氧基或丙氧基；(d)当R.sub.1为氢，R.sub.2为甲基，R.sub.3、R.sub.4、R.sub.7和R.sub.8均为氢，n为0时，R.sub.6只能是甲氧基、乙氧基或乙基；以及其治疗上可接受的盐。已发现这种化合物是有效的长效心脏抗心律失常药物，特别是通过口服途径给予。
• Design and synthesis of various 1,3,4-oxadiazoles as AChE and LOX enzyme inhibitors
  作者：Javed Iqbal、Ali Imran Mallhi、Aziz ur Rehman、Samiah H. Al-Mijalli、Mehr un-Nisa、Fatiqa Zafar、Sohail Shahzad、Shahid Rasool、Munawar Iqbal、Syed Adnan Ali Shah

  DOI：10.1515/hc-2022-0169

  日期：2023.11.15

  N-Substituted-2-propanamide analogues of 1,3,4-oxadiazole have been synthesized using a multi-step synthetic protocol to explore new therapeutic anti-enzymatic agents. Herein, we have merged sulfonyl, piperidine, oxadiazole and amide into a single unit to synthesize a library of unique compounds, 8a–n. The molecular structures of all synthesized compounds were verified by ¹³C-NMR, ¹H-NMR, HRMS and IR spectroscopy. Furthermore, the compounds were screened for their inhibition potential against acetylcholinesterase (AChE), urease and lipoxygenase (LOX) enzymes. A considerable inhibition potential was observed for three compounds against LOX with quercetin as a reference standard, two compounds against urease with thiourea as a reference standard and two compounds against AChE with eserine as a reference standard. Through molecular docking investigations, we were able to correlate the overall impact and inhibition criteria by the structure–activity relationship via the interactions between synthesized compounds and active sites of enzymes. Pharmacodynamics, pharmacokinetics and in vivo studies may be investigated further for the most active compounds to substantiate them as potential anti-enzymatic medications.

  摘要 我们采用多步合成方案合成了 1,3,4-噁二唑的 N-取代-2-丙酰胺类似物，以探索新的抗酶治疗药物。在这里，我们将磺酰基、哌啶基、噁二唑基和酰胺基合并为一个单元，合成了一个独特的化合物库 8a-n。通过 13C-NMR、1H-NMR、HRMS 和 IR 光谱验证了所有合成化合物的分子结构。此外，还筛选了这些化合物对乙酰胆碱酯酶（AChE）、脲酶和脂氧合酶（LOX）的抑制潜力。结果表明，以槲皮素为参照标准，三个化合物对 LOX 有相当大的抑制潜力；以硫脲为参照标准，两个化合物对脲酶有抑制潜力；以丝氨酸为参照标准，两个化合物对 AChE 有抑制潜力。通过分子对接研究，我们能够通过合成化合物与酶活性位点之间的相互作用，以结构-活性关系来关联整体影响和抑制标准。我们可能会对最具活性的化合物进行进一步的药效学、药代动力学和体内研究，以证实它们是潜在的抗酶药物。