3-(二甲基氨基)-1-(3-甲氧苯基)丙-1-酮盐酸盐 | 53342-08-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(二甲基氨基)-1-(3-甲氧苯基)丙-1-酮盐酸盐
• 英文名称: 3-dimethylamino-1-(3-methoxyphenyl)-propan-1-one hydrochloride
• 英文别名: [3-(3-Methoxyphenyl)-3-oxopropyl]-dimethylazanium;chloride；[3-(3-methoxyphenyl)-3-oxopropyl]-dimethylazanium;chloride
• CAS: 53342-08-8
• 化学式: C₁₂H₁₇NO₂*ClH
• 分子量: 243.733
• InChiKey: GOLJIZFBSRNXAP-UHFFFAOYSA-N

物化性质

• 熔点：
  161-162 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(二甲基氨基)-1-(3-甲氧苯基)丙-1-酮盐酸盐 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 3.0h， 生成 1-(3-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Dimmock; Shyam; Smith, Pharmazie, 1984, vol. 39, # 7, p. 467 - 470

  摘要：

  DOI：
• 作为产物：
  描述：

  聚合甲醛 、 盐酸二甲胺 、 3-甲氧基苯乙酮 以 乙醇 为溶剂， 反应 3.0h， 以24%的产率得到3-(二甲基氨基)-1-(3-甲氧苯基)丙-1-酮盐酸盐
  参考文献：
  名称：

  β-氨基酮作为1型甲硫氨酸氨基肽酶选择性不可逆抑制剂的前药

  摘要：

  我们鉴定并表征了β-氨基酮作为不可逆MetAP抑制剂的前药，这些抑制剂对MetAP-1亚型具有选择性。具有某些结构特征的β-氨基酮在生理条件下会形成α，β-不饱和酮，这些酮共价且选择性地与MetAP-1 S1口袋中的半胱氨酸结合。通过X射线晶体学和用来自大肠杆菌，金黄色葡萄球菌和两种人同工型的MetAP的测定证实了结合模式。最初鉴定的四氢萘酮衍生物对大肠杆菌MetAP相对于人MetAP-1和MetAP-2具有完全的选择性。茚满酮类似物的合理设计产生对人类1型与人类2 MetAP具有选择性的化合物。

  DOI：

  10.1016/j.bmcl.2014.09.047

文献信息

• Synthesis of new 3-aryl-4,5-dihydropyrazole-1-carbothioamide derivatives. An investigation on their ability to inhibit monoamine oxidase
  作者：E. Maccioni、S. Alcaro、F. Orallo、M.C. Cardia、S. Distinto、G. Costa、M. Yanez、M.L. Sanna、S. Vigo、R. Meleddu

  DOI：10.1016/j.ejmech.2010.07.009

  日期：2010.10

  investigate their monoamine oxidase inhibitory activity. The chemical structures of the compounds have been characterized by means of their IR, 1H NMR, 13C NMR spectroscopic data and elemental analyses. All the active compounds showed a selective activity towards the B isoform of the enzyme, regardless of the substitution on the heterocyclic ring. The inhibition of the enzymatic activity was measured on

  为了研究它们对单胺氧化酶的抑制活性，已经合成了一些不同取代的3-芳基-4,5-二氢吡唑-1-碳硫代酰胺。化合物的化学结构已通过其IR，1 H NMR，13 C NMR光谱数据和元素分析进行了表征。不论杂环上的取代如何，所有活性化合物均显示出对酶B同工型的选择性活性。测定了在杆状病毒感染的BTI昆虫细胞中表达的人重组MAO同工型对酶活性的抑制。进行对接实验的目的是合理化抑制最具活性和选择性的化合物的机理。
• Redox Series of Cyclometalated Nickel Complexes [Ni((R)Ph(R′)bpy)Br]^+/0/–/2– (H–(R)Ph(R′)bpy = Substituted 6-Phenyl-2,2′-bipyridine)
  作者：Aaron Sandleben、Nicolas Vogt、Gerald Hörner、Axel Klein

  DOI：10.1021/acs.organomet.8b00559

  日期：2018.10.8

  New organonickel complexes [Ni((R)Ph(R′)bpy)Br] carrying various substituted derivatives of the tridentate –C∧N∧N ligand 6-(phenyl-2-ide)-2,2′-bipyridine (−Phbpy) were synthesized from the precursor [Ni(COD)2] (COD = 1,5-cyclooctadiene) and the protoligands (ligand precursors) Br–(R)Ph(R′)bpy. Several synthetic routes for the protoligands were studied and compared. All new compounds have been analyzed

  新有机镍配合物[镍（（R）PH（R'）联吡啶）BR]携带三齿的各种取代的衍生物- Ç ∧ Ñ ∧ Ñ配体6-（苯基-2- IDE）-2,2'-联吡啶（- Phbpy）是由前体[Ni（COD）2]（COD = 1,5-环辛二烯）和原配体（配体前体）Br–（R）Ph（R'）bpy。对原配体的几种合成途径进行了研究和比较。所有新化合物均经过分析和光谱表征。从几种配合物中，通过XRD实验获得了晶体和分子结构。紫外可见吸收光谱和详细的电化学测量揭示了各种取代基对络合物电子结构的影响。量子化学DFT计算说明了最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）的组成，并支持将单电子还原和氧化产物指定为bpy局部配体自由基物种和瞬态镍（III）中间体， 分别。
• Beta-aminoketones as prodrugs for selective irreversible inhibitors of type-1 methionine aminopeptidases
  作者：Markus Altmeyer、Eberhard Amtmann、Carina Heyl、Aline Marschner、Axel J. Scheidig、Christian D. Klein

  DOI：10.1016/j.bmcl.2014.09.047

  日期：2014.11

  irreversible MetAP inhibitors that are selective for the MetAP-1 subtype. β-Aminoketones with certain structural features form α,β-unsaturated ketones under physiological conditions, which bind covalently and selectively to cysteines in the S1 pocket of MetAP-1. The binding mode was confirmed by X-ray crystallography and assays with the MetAPs from Escherichia coli, Staphylococcus aureus and both human isoforms

  我们鉴定并表征了β-氨基酮作为不可逆MetAP抑制剂的前药，这些抑制剂对MetAP-1亚型具有选择性。具有某些结构特征的β-氨基酮在生理条件下会形成α，β-不饱和酮，这些酮共价且选择性地与MetAP-1 S1口袋中的半胱氨酸结合。通过X射线晶体学和用来自大肠杆菌，金黄色葡萄球菌和两种人同工型的MetAP的测定证实了结合模式。最初鉴定的四氢萘酮衍生物对大肠杆菌MetAP相对于人MetAP-1和MetAP-2具有完全的选择性。茚满酮类似物的合理设计产生对人类1型与人类2 MetAP具有选择性的化合物。
• Facile synthesis of novel benzotriazole derivatives and their antibacterial activities
  作者：Jun Wan、Peng-Cheng Lv、Na-Na Tian、Hai-Liang Zhu

  DOI：10.1007/s12039-010-0094-8

  日期：2010.7

  A series of benzotriazole derivatives (compounds 1–27) were synthesized, and 24 (compounds 1–5, 9–27) of which were first reported. Their chemical structures were confirmed by means of 1H NMR, IR and elemental analyses, coupled with one selected single crystal structure (compound 1). All the compounds were assayed for antibacterial activities against three Gram positive bacterial strains (Bacillus subtilis, Staphylococcus aureus and Streptococcus faecalis) and three Gram negative bacterial strains (Escherichia coli, Pseudomonas aeruginosa and Enterobacter cloacae) by MTT method. Among the compounds tested, most of them exhibited potent antibacterial activity against the six bacterial strains. Most importantly, compound 3-benzotriazol-1-yl-1-(4-bromo-phenyl)-2-[1,2,4]triazol-1-ylpropan-1-one (19) showed the most favourable antibacterial activity against B. subtilis, S. aureus, S. faecalis, P. aeruginosa, E. coli and E. cloacae with MIC of 1.56 µg/mL, 1.56 µg/mL, 1.56 µg/mL, 3.12 µg/mL, 6.25 µg/mL and 6.25 µg/mL, respectively.

  合成了一系列苯并三唑衍生物（化合物 1-27），其中 24 种（化合物 1-5、9-27）为首次报道。通过 1H NMR、IR 和元素分析确认了这些化合物的化学结构，并选定了一个单晶结构（化合物 1）。采用 MTT 法检测了所有化合物对三种革兰氏阳性细菌菌株（枯草杆菌、金黄色葡萄球菌和粪链球菌）和三种革兰氏阴性细菌菌株（大肠杆菌、铜绿假单胞菌和泄殖腔肠杆菌）的抗菌活性。在测试的化合物中，大多数化合物都对六种细菌菌株具有很强的抗菌活性。最重要的是，化合物 3-苯并三唑-1-基-1-(4-溴苯基)-2-[1,2,4]三唑-1-基丙-1-酮（19）对枯草杆菌、金黄色葡萄球菌、粪肠球菌表现出最有利的抗菌活性。金黄色葡萄球菌、粪肠球菌、铜绿假单胞菌、大肠杆菌和泄殖腔大肠杆菌的抗菌活性最强，其 MIC 值分别为 1.56 µg/mL、1.56 µg/mL、1.56 µg/mL、3.12 µg/mL、6.25 µg/mL 和 6.25 µg/mL。
• Isochromanone-based urotensin-II receptor agonists
  作者：Fredrik Lehmann、Erika A. Currier、Roger Olsson、Uli Hacksell、Kristina Luthman

  DOI：10.1016/j.bmc.2005.01.056

  日期：2005.4

  A series of analogues of the selective non-peptide urotensin II (UII) receptor agonist 3-(4-chlorophenyl)-3-(2-dimethylaminoethyl)-isochroman- 1-one (AC-7954, 1) was synthesized and evaluated for UII agonist activity using a functional cell-based assay. The introduction of a methyl group in the 4-position resulted in a complete loss of activity, whereas substituents in the aromatic rings were beneficial. Sterically demanding amino groups were also detrimental to the activity. Several potent agonists were identified, six compounds being equally or more potent than 1. The most potent compound in the series was the 6,7-dimethyl analogue of 1 (16, pEC(50) 6.87). The racemate of 16 was resolved into the pure enantiomers using preparative straight phase HPLC. It was shown that the potency resides in the (+)-enantiomer (pEC(50) 7.11). The synthesized compounds seem to be selective for the UII receptor as no activities were observed at the closely related SSTR3 and 5 receptors. (c) 2005 Elsevier Ltd. All rights reserved.