4-(3-(1,3-dioxoisoindolin-2-yl)propoxy)benzaldehyde | 73279-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-(3-(1,3-dioxoisoindolin-2-yl)propoxy)benzaldehyde
• 英文别名: 4-(3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propoxy)-benzaldehyde；2-[3-[4-Formylphenoxy]propyl]-1H-isoindole-1,3-dione；4-[3-(1,3-Dioxoisoindol-2-yl)propoxy]benzaldehyde
• CAS: 73279-02-4
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: WACIDFSJZAPASS-UHFFFAOYSA-N

物化性质

• 熔点：
  131-132 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  511.9±30.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-(1,3-dioxoisoindolin-2-yl)propoxy)benzaldehyde 在 sodium tetrahydroborate 、 4 A molecular sieve 、 一水合肼 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 ((3-(4-(((2-(3-(((tert-butoxy)carbonyl)amino)propoxy)benzoyl)(6-phenoxy-2-benzothiazolyl)amino)methyl)phenoxy)propyl)carbonimidoyl)-bis-carbamic acid bis(tert-butyl) ester
  参考文献：
  名称：

  Synthesis and biological evaluation of nonpeptide mimetics of ω-conotoxin GVIA

  摘要：

  A benzothiazole-derived compound (4a) designed to mimic the C-alpha-C-beta bond vectors and terminal functionalities of Lys2, TyrI3 and Arg17 in omega-conotoxin GVIA was synthesised, together with analogues (4b-d), which had each side-chain mimic systematically truncated or eliminated. The affinity of these compounds for rat brain N-type and P/Q-type voltage gated calcium channels (VGCCs) was determined. In terms of N-type channel affinity and selectivity, two of these compounds (4a and 4d) were found to be highly promising, first generation mimetics of omega-conotoxin. The fully functionalised mimetic (4a) showed low PM binding affinity to N-type VGCCs (IC50 = 1.9 muM) and greater than 20-fold selectivity for this channel sub-type over P/Q-type VGCCs, whereas the mimetic in which the guanidine-type side chain was truncated back to an amine (4d, IC50 = 4.1 muM) showed a greater than 25-fold selectivity for the N-type channel. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.040
• 作为产物：
  描述：

  邻苯二甲酸亚胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 16.0h， 生成 4-(3-(1,3-dioxoisoindolin-2-yl)propoxy)benzaldehyde
  参考文献：
  名称：

  Discovery of imidazopyridines containing isoindoline-1,3-dione framework as a new class of BACE1 inhibitors: Design, synthesis and SAR analysis

  摘要：

  Alzheimer's disease is characterized by chronic neurodegeneration leading to dementia. The main cause of neurodegeneration is considered to be the accumulation of amyloid-beta. Inhibiting BACE1 is a well studied approach to lower the burden of amyloid-beta aggregates. We designed a series of imidazopyridines-based compounds bearing phthalimide moieties as inhibitors of BACE1. The compounds 8a-o were synthesized by the Groebke Blackburn Bienayme three-component reaction of heteroaromatic amidines, aldehydes and isocyanides. Evaluating the BACE1 inhibitory effects of the synthesized compounds revealed that introducing an aminocyclohexyl moiety in the imidazopyridine core resulted in a significant improvement in its BACE1 inhibitory potential. In this regard, compound 8e was the most potent against BACE1 with an IC50 value of 2.84 (+/- 0.95) mu M. Molecular docking revealed that the nitrogen atom of imidazopyridines and the oxygen atom of the phenoxypropyl linker were involved in hydrogen bound interactions with Asp228 and Asp32 of BACE1 active site, respectively. The phthalimide moiety oriented toward the flap pocket and interacted with phe108, 11e110, Trp115, 11e118 through van der Waal's and hydrophobic interactions. These findings demonstrate that imidazopyridines-based compounds bearing phthalimide moiety have the potential to decrease amyloid-beta levels and ameliorate the symptoms of Alzheimer's disease. (C) 2017 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2017.06.040

文献信息

• 1,2,4-Triazole-3,5-diamine derivatives
  申请人：Glaxo Group Limited

  公开号：US04318913A1

  公开（公告）日：1982-03-09

  The invention relates to compounds of the formula (I) ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof, in which R.sub.1 and R.sub.2 represent hydrogen, an aliphatic or cycloaliphatic group, or R.sub.1 and R.sub.2 together with the nitrogen atom form a 5 to 10 membered heterocyclic ring: Alk represents a straight or branched alkylene chain; Q represents furan, thiophen or benzene ring which is incorporated into the rest of the molecule; X represents --CH.sub.2 --, ##STR2## --O-- or --S-- where R.sub.6 represents hydrogen or methyl; n represents zero, 1 or 2; m represents 2, 3 or 4; R.sub.3 represents hydrogen, a substituted or unsubstituted aliphatic or aryl group and; R.sub.4 and R.sub.5, which may be the same or different, each represent hydrogen, a substituted or unsubstituted aliphatic, aryl, or together with the nitrogen atom form a heterocyclic group.

  该发明涉及式(I)的化合物及其生理上可接受的盐、水合物和生物前体，其中R.sub.1和R.sub.2代表氢、脂肪族或环脂族基团，或者R.sub.1和R.sub.2与氮原子一起形成5到10元杂环环：Alk代表直链或支链烷基链；Q代表噻吩或苯环，其嵌入到分子的其余部分中；X代表--CH.sub.2 --，--O--或--S--，其中R.sub.6代表氢或甲基；n代表零、1或2；m代表2、3或4；R.sub.3代表氢、取代或未取代的脂肪族或芳基团；R.sub.4和R.sub.5，可以相同也可以不同，每个代表氢、取代或未取代的脂肪族、芳基，或者与氮原子一起形成杂环基团。
• Antineoplastic .alpha.-methylene-.gamma.-butyrolactones
  申请人：National Science Council (Taiwan)

  公开号：US05962460A1

  公开（公告）日：1999-10-05

  The present invention provides antineoplastic .alpha.-methylene-.gamma.-butyrolactones represented by the general formula \x9bI! wherein R.sub.1 is a phenyl group optionally substituted with one or two groups selected from the group consisting of halide, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, phenyl, nitro and amino;.sub.2 R represents hydrogen, halide, (C.sub.1 -C.sub.4)alkyl or benzyl; X represents N; or wherein R.sub.1 is a phenyl group optionally substituted with one or two groups selected from the group consisting of halide, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4) alkoxy, nitro and amino; R.sub.2 represents Cl, F, or benzyl; X represents CH. These .alpha.-methylene-.gamma.-butyrolactones may be administered with an inert diluent or with a pharmaceutically acceptable carrier in controlling the growth of a neoplasm in a patient afflicted with a neoplasm disease. ##STR1##

  本发明提供了一种抗肿瘤的α-亚甲基-γ-丁内酯，其通式表示为\x9bI!其中R.sub.1是一个苯基，可选地取代为卤素、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)烷氧基、苯基、硝基和氨基中的一种或两种基团；R代表氢、卤素、(C.sub.1 -C.sub.4)烷基或苄基；X代表N；或其中R.sub.1是一个苯基，可选地取代为卤素、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)烷氧基、硝基和氨基中的一种或两种基团；R.sub.2代表Cl、F或苄基；X代表CH。这些α-亚甲基-γ-丁内酯可以与惰性稀释剂或药用可接受的载体一起使用，以控制患有肿瘤疾病的患者体内肿瘤的生长。
• Boron-dipyrromethene derivatives bearing N-alkyl phthalimide and amine substituents of potential application in the photoinactivation of bacteria
  作者：Jaroslaw Piskorz、Jolanta Dlugaszewska、Weronika Porolnik、Anna Teubert、Jadwiga Mielcarek

  DOI：10.1016/j.dyepig.2020.108322

  日期：2020.7

  Gram-negative rods of Escherichia coli. Novel BODIPY derivatives showed promising inactivation efficiency on S. aureus, with the highest activity for iodinated derivative, which reduced the number of bacteria by 3.6 logs10 at low 0.5 μM concentration. However, none of the tested derivatives showed a satisfactory ability to eradicate E. coli. Only non-iodinated derivative with amine substituent, at high concentrations

  合成了具有N-烷基邻苯二甲酰亚胺和胺取代基的新型硼二吡咯亚甲基衍生物，包括碘化衍生物，并使用UV-Vis分光光度法，质谱（HRMS）和NMR光谱进行了表征。非碘化类似物揭示了与荧光量子产率（Φ高发射性能˚F 0.48和0.58之间）。但单线态氧生成的量子产率（Φ Δ）与在0.01-0.06范围内的值是低的。碘化衍生物显示较强的重原子效应导致红移吸收和发射带，荧光淬灭与Φ ˚F的约0.02的值，但具有优良的Φ增加单线态氧生成的能力Δ甲醇和乙醇中的分别为0.97和0.85。在金黄色葡萄球菌革兰氏阳性球菌和大肠杆菌革兰氏阴性棒上评估了体外光动力灭活活性。新型BODIPY衍生物在金黄色葡萄球菌上显示出令人鼓舞的灭活效率，对碘化衍生物具有最高活性，在低0.5μM的浓度下，细菌数量减少了3.6 log 10。然而，没有一种测试的衍生物显示出令人满意的根除大肠杆菌的能力。只有高浓度的具有胺取代基的非碘化衍生物在log
• Template-driven self-assembly of a porphyrin-containing supramolecular complex
  作者：John S. Manka、David S. Lawrence

  DOI：10.1021/ja00162a066

  日期：1990.3

  synthesized a porphyrin encased within a protective barrier that is circumscribed by a hydrophobic groove. The tetraamino porphyrin (prepared in three steps from p-hydroxybenzaldehyde) forms an inclusion complex upon exposure to 10 equiv of heptakis (2,6-di-O-methyl)-β-cyclodextrin in aqueous solution at pH 6.0

  血红素依赖性蛋白参与多种生化现象，包括氧运输（血红蛋白）和激活（细胞色素 P-450 酶）。这些物种的类蛋白附属物充当阻止 μ-氧代寡聚体形成的空间障碍，作为防止卟啉外围氧化分解的保护屏障，作为血红素的水溶性载体，以及作为维持疏水性的实体根据活性位点的性质，我们合成了一种卟啉，它被包裹在一个由疏水凹槽包围的保护屏障中。四氨基卟啉（由对羟基苯甲醛分三步制备）在暴露于 pH 6.0 的 10 当量七（2,6-二-O-甲基）-β-环糊精水溶液时形成包合物
• [EN] CRYPTATE COMPOUNDS<br/>[FR] COMPOSÉS CRYPTATES
  申请人：AUSTRALIAN NUCLEAR SCIENCE TEC

  公开号：WO2013003912A1

  公开（公告）日：2013-01-10

  Disclosed herein is a method for coupling a first compound having the formula (I) with a second compound that contains a carbonyl group. Also disclosed herein are compounds that can be formed by this method, and uses for such compounds.

  本文公开了一种将具有式(I)的第一化合物与含有羰基基团的第二化合物耦合的方法。本文还公开了可以通过此方法形成的化合物以及这些化合物的用途。