N-(4-fluorobenzyl)-1,3-diaminopropane | 97146-01-5

• 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: N-(4-fluorobenzyl)-1,3-diaminopropane
• 英文别名: N¹-(4-fluorobenzyl)propane-1,3-diamine；N-(4-fluorobenzyl)propane-1,3-diamine；N'-[(4-fluorophenyl)methyl]propane-1,3-diamine
• CAS: 97146-01-5
• 化学式: C₁₀H₁₅FN₂
• mdl: MFCD12803459
• 分子量: 182.241
• InChiKey: NDENKGKOZFIGOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-fluorobenzyl)-1,3-diaminopropane 在 六氯环三磷腈 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 62.0h， 生成 7-(4-fluorobenzyl)-2,2,4,4-tetrapyrrolidin-1-yl-1,3,5,7,11-pentaaza-2λ5,4λ5,6λ5-triphosphaspiro[5.5]unideca-1,3,5-triene
  参考文献：
  名称：

  Phosphorus–nitrogen compounds part 22. Syntheses, structural investigations, biological activities and DNA interactions of new mono and bis (4-fluorobenzyl) spirocyclophosphazenes

  摘要：

  The reactions of hexachlorocyclotriphosphazene, N3P3Cl6, with mono (1 and 2) and bis(4-fluorobenzyl) diamines (3-5), FPhCH2NH(CH2)(n)NHR (R=H or FPhCH2-), produce mono (1a and 2a) and bis(4-fluorobenzyl) monospirocyclophosphazenes (3a-5a). The tetraaminomonospirocyclophosphazenes (1b-2d) are obtained from the reactions of the partly substituted phosphazenes (1a and 2a) with excess pyrrolidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD), respectively. The tetrachlorobis(4-fluorobenzyl) monospirocyclophosphazenes (4a and 5a) with excess pyrrolidine, morpholine and DASD afford the fully substituted bis(4-fluorobenzyl) monospirocyclophosphazenes (4b, 4d-5d) in boiling THF. In addition, monochlorobis(4-fluorobenzyl) monospirocyclophosphazenes (4e and 41) have also been isolated from the reactions with excess morpholine and DASD in boiling THF. The structural investigations of the compounds have been verified by elemental analyses, MS. FTIR, H-1, C-13, F-19 (for 1d and 2d). P-31 NMR, HSQC and HMBC techniques. The crystal structures of 3a, 4a, 5a and 2b have been determined by X-ray crystallography. The compounds 2a-5a, 1b-2d, 4b, 4d-5d, 4e and 41 have been screened for antibacterial effects on bacteria and for antifungal activity against yeast strains. The compounds 1b and 4b showed antimicrobial activity against three species of bacteria, Bacillus subtilis, Bacillus cereus and Staphylococcus aureus, and two fungi, Candida albicans and Candida tropicalis. Minimum inhibitory concentrations (MIC) were determined for 1b and 4b. The MIC values were found to be 5000 mu M for each bacteria. The most effective compound, 4b has exhibited activity with a MIC of 312 mu M for C albicans and 625 mu M for C. tropicalis. DNA-binding and the nature of the interaction with pBR322 plasmid DNA are studied. All of the compounds induce changes on the DNA mobility and intensity. Prevention of Hind[l] digestion with the compounds indicates that the compounds bind with AT nucleotides in DNA. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.08.035
• 作为产物：
  描述：

  3-[(4-fluorophenyl)methylideneamino]propan-1-amine 在 reducting agent 作用下， 生成 N-(4-fluorobenzyl)-1,3-diaminopropane
  参考文献：
  名称：

  Phosphorus–nitrogen compounds part 22. Syntheses, structural investigations, biological activities and DNA interactions of new mono and bis (4-fluorobenzyl) spirocyclophosphazenes

  摘要：

  The reactions of hexachlorocyclotriphosphazene, N3P3Cl6, with mono (1 and 2) and bis(4-fluorobenzyl) diamines (3-5), FPhCH2NH(CH2)(n)NHR (R=H or FPhCH2-), produce mono (1a and 2a) and bis(4-fluorobenzyl) monospirocyclophosphazenes (3a-5a). The tetraaminomonospirocyclophosphazenes (1b-2d) are obtained from the reactions of the partly substituted phosphazenes (1a and 2a) with excess pyrrolidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD), respectively. The tetrachlorobis(4-fluorobenzyl) monospirocyclophosphazenes (4a and 5a) with excess pyrrolidine, morpholine and DASD afford the fully substituted bis(4-fluorobenzyl) monospirocyclophosphazenes (4b, 4d-5d) in boiling THF. In addition, monochlorobis(4-fluorobenzyl) monospirocyclophosphazenes (4e and 41) have also been isolated from the reactions with excess morpholine and DASD in boiling THF. The structural investigations of the compounds have been verified by elemental analyses, MS. FTIR, H-1, C-13, F-19 (for 1d and 2d). P-31 NMR, HSQC and HMBC techniques. The crystal structures of 3a, 4a, 5a and 2b have been determined by X-ray crystallography. The compounds 2a-5a, 1b-2d, 4b, 4d-5d, 4e and 41 have been screened for antibacterial effects on bacteria and for antifungal activity against yeast strains. The compounds 1b and 4b showed antimicrobial activity against three species of bacteria, Bacillus subtilis, Bacillus cereus and Staphylococcus aureus, and two fungi, Candida albicans and Candida tropicalis. Minimum inhibitory concentrations (MIC) were determined for 1b and 4b. The MIC values were found to be 5000 mu M for each bacteria. The most effective compound, 4b has exhibited activity with a MIC of 312 mu M for C albicans and 625 mu M for C. tropicalis. DNA-binding and the nature of the interaction with pBR322 plasmid DNA are studied. All of the compounds induce changes on the DNA mobility and intensity. Prevention of Hind[l] digestion with the compounds indicates that the compounds bind with AT nucleotides in DNA. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.08.035

文献信息

• [EN] NEW-4-(PYRROLOPYRIMIDIN-6-YL)BENZENESULPHONAMIDE DERIVATIVES<br/>[FR] NOUVEAUX DERIVES DE 4-(PYRROLOPYRIMIDIN-6-YL)BENZENESULPHONAMIDE
  申请人：ALMIRALL PRODESFARMA SA

  公开号：WO2003082873A1

  公开（公告）日：2003-10-09

  This invention is directed to new potent and selective antagonists of A2A and/or A2B adenosine receptors having the general formula (I) to process for their preparation; to pharmaceutical compositions comprising them; and to their use in therapy.

  这项发明是针对新型高效选择性A2A和/或A2B腺苷受体拮抗剂的，其具有通用公式（I），用于其制备的过程；包含它们的药物组合物；以及它们在治疗中的应用。
• Phosphorus–nitrogen compounds: part 70. Syntheses of tetraaminomono/bis(4-fluorobenzyl)spiro(<i>N</i>/<i>N</i>)cyclotriphosphazenes: structural characterization, Hirshfeld surface analysis and comparative evaluation of esterase activities of hCA I and hCA II isoenzymes
  作者：Aytuğ Okumuş、Gamze Elmas、Arzu Binici、Ekrem Tunca、Tuncer Hökelek、Zeynel Kılıç

  DOI：10.1039/d3nj00721a

  日期：——

  data identified the structures of the new products. In addition, the solid-state structure of 2b was confirmed by X-ray crystallography. Hirshfeld surface analysis of 2b indicates that the most important contributions for the crystal packing are from H⋯H (61.2%), H⋯C/C⋯H (24.8%) and H⋯F/F⋯H (9.3%) interactions. On the other hand, the inhibitory effects of these cyclotriphosphazenes on the esterase activities

  通过六氯环三磷腈、N 3 P 3 Cl 6（三聚体；HCCP ）与N -（ 4-氟苄基)-1,3-二氨基丙烷( L1 )和N , N'-双(4-氟苄基)-1,3-二氨基丙烷( L2 )。四氨基单-( 1a和1b ) 和双-(4-氟苄基)螺( N / N)环三磷腈 ( 2a和2b ) 分别由螺1和2与过量的乙基哌嗪和苯基哌嗪在沸腾的 THF 中进行缩合反应制备。元素分析、FTIR、ESI-MS、31 P、13 C 和1 H NMR 数据确定了新产品的结构。此外，通过X射线晶体学证实了2b的固态结构。2b的 Hirshfeld 表面分析表明对晶体堆积最重要的贡献来自 H⋯H（61.2%）、H⋯C/C⋯H（24.8%）和 H⋯F/F⋯H（9.3%）相互作用。另一方面，在体外研究了这些环三磷腈对 hCA I 和 hCA II 同工酶的酯酶活性的抑制作用。确定化合物2b表现出比化合物2a更强的抑制作用。
• Nitromethylen-tetrahydropyrimidin-Derivate, Verfahren zu ihrer Herstellung sowie insektizide, mitizide, tickizide und nematizide Mittel
  申请人：NIHON TOKUSHU NOYAKU SEIZO K.K.

  公开号：EP0136636A2

  公开（公告）日：1985-04-10

  Die vorliegende Erfindung beschreibt (1) ein Nitromethylen-tetrahydropyrimidin-Derivat der allgemeinen Formel (I) in der X für Halogen steht, (2) Verfahren zur Herstellung des Nitromethylen-tetrahydropyrimidin-Derivats der allgemeinen Formel (I), (3) insektizide, mitizide und nematizide Mittel, die als Wirkstoff das Nitromethylen-tetrahydropyrimidin-Derivat der allgemeinen Formel (I) enthalten, und (4) ein Verfahren zur Bekämpfung schädlicher Insekten, Milben oder Zecken und Nematoden, bei dem das Nitromethylen-tetrahydropyrimidin-Derivat der allgemeinen Formel (I) entweder allein oder in Kombination mit Verdünnungsmittel (einem Lösungsmittel und/oder einem Streckmittel und/oder einem Träger) und/oder einem oberflächenaktiven Mittel und, falls weiterhin erforderlich, einem Stabilisator, einem Haftmittel und einem synergistischen Mittel zur Einwirkung gebracht wird.

  本发明描述了 (1) 通式(I)的硝基亚甲基四氢嘧啶衍生物 其中 X 代表卤素、 (2) 通式(I)的硝基亚甲基四氢嘧啶衍生物的制备工艺、 (3) 含有通式（I）的硝基亚甲基四氢嘧啶衍生物作为活性成分的杀虫、杀螨剂和杀线虫剂，以及 (4) 一种控制有害昆虫、螨虫或蜱虫和线虫的方法，其中通式(I)的硝基亚甲基四氢嘧啶衍生物可单独或与稀释剂（溶剂和/或扩展剂和/或载体）和/或表面活性剂以及（如有进一步需要）稳定剂、粘合剂和增效剂一起发挥作用。
• Aminoalcohol lipidoids and uses thereof
  申请人：Massachusetts Institute of Technology

  公开号：US10844028B2

  公开（公告）日：2020-11-24

  Aminoalcohol lipidoids are prepared by reacting an amine with an epoxide-terminated compound are described. Methods of preparing aminoalcohol lipidoids from commercially available starting materials are also provided. Aminoalcohol lipidoids may be prepared from racemic or stereochemically pure epoxides. Aminoalcohol lipidoids or salts forms thereof are preferably biodegradable and biocompatible and may be used in a variety of drug delivery systems. Given the amino moiety of these aminoalcohol lipidoid compounds, they are particularly suited for the delivery of polynucleotides. Complexes, micelles, liposomes or particles containing the inventive lipidoids and polynucleotide have been prepared. The inventive lipidoids may also be used in preparing microparticles for drug delivery. They are particularly useful in delivering labile agents given their ability to buffer the pH of their surroundings.

  本文介绍了通过胺与环氧化物封端化合物反应制备氨基醇脂质的方法。还提供了从市售起始原料制备氨基醇类脂质的方法。氨基醇脂质可由外消旋或立体化学纯环氧化物制备。氨基醇类脂质或其盐类最好具有生物降解性和生物相容性，可用于各种给药系统。考虑到这些氨基醇类脂化合物的氨基，它们特别适合用于多核苷酸的给药。现已制备出含有本发明类脂化合物和多核苷酸的复合物、胶束、脂质体或颗粒。本发明的类脂质还可用于制备给药微粒。由于本发明脂质具有缓冲周围环境 pH 值的能力，因此在递送易变药剂方面特别有用。
• NEW-4-(PYRROLOPYRIMIDIN-6-YL)BENZENESULPHONAMIDE DERIVATIVES
  申请人：Laboratorios Almirall, S.A.

  公开号：EP1492793B1

  公开（公告）日：2008-01-16