N-(4-氨基-1-丁基)邻苯二甲酰亚胺盐酸盐 | 35517-18-1

• 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
• 中文名称: N-(4-氨基-1-丁基)邻苯二甲酰亚胺盐酸盐
• 英文名称: N-(4-aminobutyl)phthalimide hydrochloride
• 英文别名: 2-(4-aminobutyl)-2,3-dihydro-1H-isoindole-1,3-dione hydrochloride；2-(4-aminobutyl)isoindole-1,3-dione;hydrochloride
• CAS: 35517-18-1
• 化学式: C₁₂H₁₄N₂O₂*ClH
• mdl: MFCD18483316
• 分子量: 254.716
• InChiKey: RFOHHXVSYWABJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  63.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-氨基-1-丁基)邻苯二甲酰亚胺盐酸盐 在 sodium hydride 、 sodium carbonate 、 三乙胺 、 sodium iodide 、 sodium nitrite 作用下， 以 四氯化碳 、 二氯甲烷 、 乙酸酐 、 溶剂黄146 、 丙酮 为溶剂， 反应 49.0h， 生成 ethyl 2-carbethoxy-2,6-diphthalimidohexanoate
  参考文献：
  名称：

  链丝菌素 F 的生物合成。 5. 链霉菌 L-1689-23 形成 β-赖氨酸

  摘要：

  链丝菌素 F 的 ..β..-赖氨酸部分的形成已通过喂食链霉菌 L-1689-23 ..cap alpha..-(3-/sup 13/C,/sup 15/N)- 、..cap alpha..-((3RS)-/sup 2/H/sub 2/)-、..cap alpha..-((3R)-/sup 2/H)-和..cap alpha ..-((3S)-/sup 2/H)赖氨酸和..β..-((2S)-/sup 2/H)赖氨酸。通过对衍生抗生素的 /sup 13/C NMR 或 /sup 2/H NMR 谱的分析，已确定 ..cap α..-氮迁移到 C-3 并通过构型反转分子内过程，并且 3-pro-R 氢迁移到 C-2，通过基本上或完全分子间的过程进行构型反转。标记的 ..β..-赖氨酸的高度掺入表明它可能是链丝菌素 F 生物合成的中间体。

  DOI：

  10.1021/ja00354a047
• 作为产物：
  描述：

  N-(4-溴丁基)邻苯二甲酰亚胺 在 palladium dihydroxide 盐酸 、 sodium azide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 57.0 ℃ 、220.64 kPa 条件下， 反应 52.0h， 生成 N-(4-氨基-1-丁基)邻苯二甲酰亚胺盐酸盐
  参考文献：
  名称：

  .alpha.-Methyl polyamines: metabolically stable spermidine and spermine mimics capable of supporting growth in cells depleted of polyamines

  摘要：

  In order to assess the tolerance of the target enzyme spermine synthase for alpha-substituents on the aminopropyl moiety of the substrate spermidine, 1-methylspermidine (MeSpd, 2) was synthesized. It was determined that MeSpd is a poor substrate for spermine synthase and is not a substrate for spermidine N1-acetyltransferase, suggesting that alpha-methylated polyamines might be metabolically stable and therefore useful tools for studying polyamine effects in intact cells. On the basis of initial cellular results with 2, 1-methylspermine (MeSpm, 3) and 1,12-dimethylspermine (Me2Spm, 4) were also synthesized. When added to cells (L1210, SV-3T3, or HT29) depleted of both putrescine and spermidine by prior treatment with alpha-(difluoromethyl)ornithine (DFMO), these alpha-methylated polyamines were able to restore cell growth to that observed in the absence of DFMO. In accord with the enzyme data noted above, metabolic studies indicated a slow conversion of 2 to 3, but no metabolism of 4 in these cells. It was concluded from these results that the alpha-methylated polyamines are able to substitute for the natural polyamines spermidine and spermine in critical biochemical processes which involve polyamines for continued cell growth. In accord with the hypothesis, preliminary data indicate that MeSpd and Me2Spm are as effective as spermidine and spermine, respectively, in promoting the conversion of B-DNA to Z-DNA.

  DOI：

  10.1021/jm00082a013

文献信息

• Synthesis and properties of deoxyoligonucleotides containing putrescinylthymine (nucleosides and nucleotides. LXXVI).
  作者：TADAYUKI TAKEDA、KAZUYOSHI IKEDA、YOSHIHISA MIZUNO、TOHRU UEDA

  DOI：10.1248/cpb.35.3558

  日期：——

  Putrescinylthymidine was prepared by the reduction of the Schiff base formed from a 2'-deoxy-5-formyluridine derivative and N-phthaloylputrescine, followed by deprotection. The following deoxyoligonucleotides containing putrescinylthymine (TP) were synthesized; dodecathymidylic acids containing two to four TP residues, self-complementary decanucleotides (AAGAATTCTT) and dodecanucleotides (AGATAGCTATCT) in which T residues were partly replaced by TP, and related oligomers. Oligonucleotides containing TP were resistant to nuclease S1 digestion and were poor substrates to venom phosphodiesterase. The thermal stability (Tm) of the duplex structure of oligomers containing TP was not enhanced in spite of the expected electrostatic binding between the putrescinyl and phosphoryl residues, and was rather sequence-dependent.

  腐胺胸苷是通过从 2'-脱氧-5-甲酰尿苷衍生物和 N-邻苯二甲酰胺腐胺形成的希夫碱的还原反应制备的，随后进行去保护处理。合成了以下含有腐胺胸苷（TP）的脱氧寡核苷酸；含有两个到四个 TP 殘基的十二聚胸苷酸、自互补的十聚核苷酸（AAGAATTCTT）和十二聚核苷酸（AGATAGCTATCT），其中 T 残基部分被 TP 替代，以及相关的寡聚物。含有 TP 的寡核苷酸对核酸酶 S1 消化具抵抗性，并且是毒液磷酸二酯酶的劣质底物。尽管预计腐胺和磷酸残基之间存在静电结合，含有 TP 的寡聚物双链结构的热稳定性（Tm）并没有增强，而是相当依赖序列。
• New Ditopic and Tripodal 1,2,4-Triazole- and Tetrazole-Based Ligands for Coordination Chemistry
  作者：Yann Garcia、Yves Boland、Pascale Hertsens、Jacqueline Marchand-Brynaert

  DOI：10.1055/s-2006-926439

  日期：2006.5

  amine precursors. The first family consisted of ditopic ligands containing both 1-R-tetrazole and 4-R-1,2,4-triazole moieties linked by an alkyl spacer, white the second consists of branched ligands with three azole cycles linked to a benzene core through ether bonds. Both classes are suitable for building multidimensional polynuclear coordination assemblies and for the observation of thermal spin state

  报道了两类新的基于唑类的多面体配体的实际合成。前体胺的合成是通过用叠氮化物取代离去基团，然后用三苯膦和水还原来实现的。另一种有效的方法是使用 Mitsunobu 与邻苯二甲酰亚胺偶联，从而将伯醇转化为伯胺。通过这些胺前体的环化得到三唑和四唑。第一个家族由包含通过烷基间隔连接的 1-R-四唑和 4-R-1,2,4-三唑部分的双位配体组成，第二个家族由具有三个唑环的支链配体组成醚键。
• Somatostatin agonists and antagonists
  申请人：Novo Nordisk A/S

  公开号：US06127343A1

  公开（公告）日：2000-10-03

  The present invention relates to compounds, compositions containing them, and their use for treating medical disorders related to binding to human somatostatin receptor subtypes.

  本发明涉及化合物、含有这些化合物的组合物，以及它们用于治疗与结合到人类生长抑素受体亚型相关的医学疾病的用途。
• Use of somatostatin agonists and antagonists for treating diseases
  申请人：Novo Nordisk A/S

  公开号：US06159941A1

  公开（公告）日：2000-12-12

  The invention relates to the use of a somatostatin receptor ligand of nonpeptide origin, e.g. of the general formula Ia or Ib ##STR1## or a pharmaceutically acceptable salt thereof, which has high and/or selective affinity to the somatostatin receptor protein designated SSTR4 and, for the preparation of a medicament for the treatment of a disease associated with an adverse condition in the retina and/or iris-ciliary body of a mammal. Such conditions are high intraocular pressure (IOP) and/or deep ocular infections. The diseases which may be treated are e.g. glaucoma, stromal keratitis, iritis, retinitis, cataract and conjunctivitis.

  该发明涉及使用非肽源的生长抑素受体配体，例如一般式Ia或Ib##STR1##或其药用盐，其对生长抑素受体蛋白SSTR4具有高和/或选择性亲和力，并用于制备用于治疗哺乳动物视网膜和/或虹膜-睫状体中不良状况相关疾病的药物。这些疾病包括高眼压（IOP）和/或深部眼部感染。可以治疗的疾病包括青光眼、基质性角膜炎、虹膜炎、视网膜炎、白内障和结膜炎。
• Discovery of a new class of histone deacetylase inhibitors with a novel zinc binding group
  作者：Youxuan Li、Patrick M. Woster

  DOI：10.1039/c4md00401a

  日期：——

  Small molecules featuring a hydroxamic acid or a benzamide zinc binding group (ZBG) are the most thoroughly studied histone deacetylase (HDAC) inhibitors. However, concerns about the pharmacokinetic liabilities of the hydroxamic acid moiety and potential metabolic toxicity of the aniline portion of benzamideHDAC inhibitors have stimulated research efforts aimed at discovering alternative ZBGs. Here

  具有异羟肟酸或苯甲酰胺锌结合基团（ZBG）的小分子是研究最深入的组蛋白脱乙酰基酶（HDAC）抑制剂。但是，人们担心异羟肟酸部分的药代动力学特性和苯胺部分的潜在代谢毒性。苯甲酰胺HDAC抑制剂刺激了旨在发现替代ZBG的研究工作。在这里，我们将2-（恶唑-2-基）苯酚部分报告为新型ZBG，可用于生产作为有效HDAC抑制剂的化合物。已经合成了一系列具有这种新型ZBG的类似物，这些类似物对HDAC1和IIb类HDAC（HDAC6和HDAC10）表现出选择性抑制作用。化合物10在MV-4-11白血病细胞系中的IC 50值为7.5μM，而2.5μM的化合物10诱导了0.5μM的SAHA相当于相当数量的乙酰化组蛋白3赖氨酸9（H3K9）和p21 Waf1 / CIP1。化合物10的建模 在HDAC2的活性位点表明2-（恶唑-2-基）苯酚部分具有类似于 苯甲酰胺HDAC抑制剂。