1-(氯乙酰基)-4-(2-甲氧基苯基)哌嗪盐酸盐 | 21057-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(氯乙酰基)-4-(2-甲氧基苯基)哌嗪盐酸盐
• 中文别名: 1-(氯乙酰基)-4-(2-甲氧苯基)哌嗪；2-氯-1-[4-(2-甲氧苯基)-1-哌嗪]乙酮；2-氯-1-[4-(2-甲氧基-苯基)-哌嗪-1-基]-乙酮；2-氯-1-[4-(2-甲氧苯基)哌嗪-1-基]乙酮
• 英文名称: 4-[(2-methoxy)phenyl]-1-(2-chloroacetyl)piperazine
• 英文别名: 2-chloro-1-(4-(2-methoxyphenyl)piperazin-1-yl)ethanone；1-(chloroacetyl)-4-(2-methoxyphenyl)piperazine；1-(2-chloroacetyl)-4-(2-methoxyphenyl)piperazine；N-chloroacetyl N′-2-anisylpiperazine；2-chloro-1-[4-(2-methoxyphenyl)-1-piperazinyl]ethan-1-one；1-(2-Methoxy-phenyl)-4-chlor-acetyl-piperazin；2-Chloro-1-[4-(2-methoxy-phenyl)-piperazin-1-yl]-ethanone；2-chloro-1-[4-(2-methoxyphenyl)piperazin-1-yl]ethanone
• CAS: 21057-39-6
• 化学式: C₁₃H₁₇ClN₂O₂
• mdl: MFCD01480809
• 分子量: 268.743
• InChiKey: BEWLHPLOBQBASL-UHFFFAOYSA-N

物化性质

• 沸点：
  441.2±45.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  1-(氯乙酰基)-4-(2-甲氧基苯基)哌嗪盐酸盐 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以73%的产率得到1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine
  参考文献：
  名称：

  2-[(3-Methoxyphenylethyl)phenoxy]-Based ABCB1 Inhibitors: Effect of Different Basic Side-Chains on Their Biological Properties

  摘要：

  Recently, 2-[(3-methoxyphenylethyl)phenoxy]-moiety has been selected for the design and synthesis of new small ABCB1 inhibitors. In the present paper, this moiety has been linked through a spacer of 2-5 carbon atoms to the nitrogen of three different basic nuclei such as: (i) N-4-arylpiperazine, (ii) N-4-methylpiperazine, and (iii) 6,7-dimethoxytctrahydroisoquinoline. The results demonstrated that all the selected basic nuclei were well tolerated and that, globally, the best inhibitory activity for each series was obtained when the spacer between the 2-[(3-methoxyphenylethyl)phenoxy]moiety and the basic nucleus consisted of a four-carbon chain. Among the synthesized compounds, N-4-methylpiperazine- 10C (IC50 = 0.15 W) and tetrahydroisoquinoline-derivatives 11c (IC50 = 0.08 W) with the spacer n = 4 for both series, displayed the best potency to inhibit ABCB1 activity. Moreover, for each compound, the ABCB1 interacting mechanism has been evaluated by three combined biological assays. N-4-methylpiperazine- (10a-d) and tetrahydroisoquinoline-(11a-d) derivatives were Cyclosporin A-like ABCB1 nontransported substrates.

  DOI：

  10.1021/jm800928j
• 作为产物：
  描述：

  1-(2-甲氧苯基)哌嗪 、 氯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-(氯乙酰基)-4-(2-甲氧基苯基)哌嗪盐酸盐
  参考文献：
  名称：

  含1，4-苯并二恶烷部分的哌嗪衍生物的合成及体内抗炎性评价

  摘要：

  已经合成了六个含有1,4-苯并二恶烷部分的哌嗪衍生物6a – f，并通过1 H NMR，ESI-MS和元素分析对其进行了表征。单晶X射线衍射进一步证实了6d的结构。使用经典的对二甲苯诱导的小鼠耳肿胀模型筛选所有这些新化合物的体内抗炎活性。结果表明，大多数目标化合物均具有显着的抗炎活性，特别是在苯基哌嗪环上具有邻位取代甲氧基的化合物6a表现出最佳的活性。

  DOI：

  10.17344/acsi.2018.4887

文献信息

• Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents
  作者：Pavan K. Bangalore、Siva K. Vagolu、Rakesh K. Bollikanda、Dileep K. Veeragoni、Pallavi C. Choudante、Sunil Misra、Dharmarajan Sriram、Balasubramanian Sridhar、Srinivas Kantevari

  DOI：10.1021/acs.jnatprod.9b00475

  日期：2020.1.24

  be the most active analogue, inhibiting Mycobacterium tuberculosis (Mtb) at an MIC value of 2.5 μM. Analogues 16 and 27, with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on Bacillus subtilis, with compounds 18 [3-(trifluoromethyl)phenacyl]

  （+）-尿酸是地衣中的二次代谢产物，具有广泛的生物学特性，例如抗肿瘤，抗微生物，抗病毒，抗炎和杀虫活性。对这些药理活性感兴趣并挖掘其潜力，我们在此介绍新的松萝酸烯胺酮偶联的1,2,3-三唑10-44作为抗分枝杆菌药的合成和生物学评估。将（+）-松香酸与炔丙基胺缩合，得到具有末端乙炔基部分的松香酸烯胺酮8。在铜催化下，它进一步与各种叠氮化物A1-A35反应，以高收率得到三唑10-44。在合成的化合物中，糖精衍生物36被证明是活性最高的类似物，在MIC值为2.5μM时可抑制结核分枝杆菌（Mtb）。类似物16和27，以及3，4-二氟苯酰基和2-酰基萘单元分别在MIC值为5.4和5.3μM时抑制Mtb。在测试的革兰氏阳性和革兰氏阴性细菌中，新衍生物对枯草芽孢杆菌具有活性，化合物18 [3-（三氟甲基）苯甲酰基]和29（N-酰基吗啉基）分别显示抑制浓度41和90.7μM，而它们对其他测试细菌菌株没有
• Design, synthesis and biological profiling of aryl piperazine based scaffolds for the management of androgen sensitive prostatic disorders
  作者：Sonal Gupta、Deepti Pandey、Dhanaraju Mandalapu、Veenu Bala、Vikas Sharma、Mahendra Shukla、Santosh K. Yadav、Nidhi Singh、Swati Jaiswal、Jagdamba P. Maikhuri、Jawahar Lal、Mohammad I. Siddiqi、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1039/c6md00426a

  日期：——

  Twenty-six piperazine derivatives were synthesized and findings revealed that compound9ais promising candidate for management of prostatic disorders.

  二十六种哌嗪衍生物被合成，研究结果显示化合物9a是治疗前列腺疾病的有希望的候选药物。
• Betulinic acid derivatives: a new class of α-glucosidase inhibitors and LPS-stimulated nitric oxide production inhibition on mouse macrophage RAW 264.7 cells
  作者：Narayanarao Gundoju、Ramesh Bokam、Nageswara Rao Yalavarthi、Rajaram Azad、Mangala Gowri Ponnapalli

  DOI：10.1080/14786419.2018.1462182

  日期：2019.9.17

  Chemical manipulation studies were conducted on betulinic acid (1), twenty-one new rationally designed analogues of 1 with modifications at C-28 were synthesized for their evaluation of inhibitory effects on α-glucosidase and LPS-stimulated nitric oxide production in mouse macrophage RAW 264.7 cells. Compound 2 (IC50 = 5.4 μM) exhibited an almost 1.4-fold increase in α-glucosidase inhibitory activity

  对桦木酸（1）进行了化学操作研究，合成了二十一种经过合理设计的新的类似物1（在C-28处进行了修饰），以评估其对α-葡萄糖苷酶和LPS刺激的小鼠巨噬细胞RAW中一氧化氮生成的抑制作用264.7细胞。化合物2（IC 50 = 5.4μM）对酵母α-葡萄糖苷酶的α-葡萄糖苷酶抑制活性提高了近1.4倍，而类似物5（IC 50 16.4μM）和11（IC 50 16.6μM）增强了2倍对抑制NO产生的活性比桦木酸高。
• Synthesis and pharmacological evaluation of novel fused thiophene derivatives as 5-HT2A receptor antagonists: Molecular modeling study
  作者：Mohamed M. El-Kerdawy、Eman R. El-Bendary、Alaa A.-M. Abdel-Aziz、Dalia R. El-wasseef、Naglaa I. Abd El-Aziz

  DOI：10.1016/j.ejmech.2010.01.013

  日期：2010.5

  17 and tetrahydro-5H-cycloheptathienopyrimidin-4(3H)-ones 21 have been synthesized and tested for their 5-HT2A antagonist activity. Preliminary pharmacological studies showed that compounds 3-[2-[4-phenylpiperazin-1-yl]ethyl]-6,7-dihydro-5H-cyclopenta[b]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione 6a and ethyl 2-[[4-(2-methoxyphenyl)piperazin-1-yl]acetylamino]-4,5,6,7-tetrahydro-6-methylthieno[2,3-c]pyridine-3-carboxylate

  cyclopentathienopyrimidinediones的新型衍生物6，pyridothienopyrimidinediones 7，乙基cycloheptathiophene -3-羧酸10，乙基四氢噻吩-3-羧酸酯11，tetrahydrocycloheptathienopyrimidin-4（3 ħ） -酮12，tetrahydrotriazolobenzothienopyrimidin-5（4 ħ） -酮17和四氢-5- H -cycloheptathienopyrimidin-4（3 H）-ones 21已被合成并测试其5-HT 2A拮抗剂活性。初步药理研究表明，化合物3- [2- [4-苯基哌嗪-1-基]乙基] -6,7-二氢-5H-环戊[ b ]噻吩并[2,3 - d ]嘧啶-2,4（1 H，3 H）-二酮6a和乙基2-[[[4-（2-甲氧基苯基）哌嗪-1-基]乙酰氨基]发现-5
• Molecular design and synthesis of 1,4-disubstituted piperazines as α1-adrenergic receptor blockers
  作者：Dalal A. Abou El-Ella、Mohammed M. Hussein、Rabah A.T. Serya、Rana M. Abdel Naby、Ahmed M. Al-Abd、Dalia O. Saleh、Wafaa I. El-Eraky、Khaled A.M. Abouzid

  DOI：10.1016/j.bioorg.2014.03.005

  日期：2014.6

  A new series of 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid amide and 3,5,6,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-one derivatives were designed, synthesized, their binding and functional properties as α1-adrenoreceptors blockers were evaluated. A new validated α1-adrenoreceptor blocker pharmacophore model (hypothesis) was generated using Discovery Studio 2.5. The compare-fit

  一系列新的4,5,6,7-四氢噻吩并[2,3-c]吡啶-3-羧酸酰胺和3,5,6,8-四氢吡啶并[4'，3'：4,5]噻吩并[ 2,3-d]嘧啶-4-酮衍生物设计，合成，它们的结合和功能特性为α 1 -adrenoreceptors阻滞剂进行了评价。一种新的有效的α 1使用Discovery Studio的2.5生成肾上腺素受体阻断剂药效团模型（假说）。完成了针对具有所产生假设的设计分子的比较拟合研究，并且几种化合物显示出显着的高拟合值。化合物IVa–c，VIIa–d，VIIIa–c，Xa–c，XIa–d的阻滞活性范围为46.73％至94.74％，而哌唑嗪的阻滞活性为99.17％。