3,5-diacetyl aniline | 87533-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-diacetyl aniline
• 英文别名: 1,3-diacetyl-5-aminobenzene；3,5-bis-acetylaniline；1,1'-(5-amino-1,3-phenyl)bis(ethyl-1-one)；3,5-Diacetylaniline；1-(3-acetyl-5-aminophenyl)ethanone
• CAS: 87533-49-1
• 化学式: C₁₀H₁₁NO₂
• mdl: MFCD03423784
• 分子量: 177.203
• InChiKey: XUVYQFMQZZYSLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  3,5-diacetyl aniline 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 N-[3,5-bis[N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]acetamide;hydrochloride
  参考文献：
  名称：

  锥虫病1,3-亚芳基二酮双（胍hydr）。取代和杂环类似物之间的构效关系。

  摘要：

  基于1,3-二乙酰基苯双guan胍（4）和2,6-二乙酰基吡啶双（胍（17）的抗胰管体活性，许多取代的和杂环的1,3-亚芳基二酮双guan胍是制备并测试了针对小鼠布鲁氏锥虫感染的方法。在4的5个取代衍生物中观察到很宽的ED50值。5-氨基类似物5和5-乙酰氨基类似物6的活性约为4的两倍。1,3,5-三乙酰苯三（guan）（12）在该测试系统中，其活性约为4的9倍，活性约为目前使用的锥虫二甲基二氮杂苯乙酸乙酸盐的一半。其他5个衍生物的活性等于或低于母体化合物4的活性。三个新的杂环类似物的活性均低于2，6-二乙酰基吡啶衍生物17和苯衍生物4。邻位hydrhydr侧链的环取代总是不利于活性。侧链同系物1，3-二戊酰基苯双（胍基hydr）和1，3-二乙酰基苯双（2-咪唑啉-2-基hydr）基本上没有活性。

  DOI：

  10.1021/jm00367a007
• 作为产物：
  描述：

  5-硝基异酞酰氯 在 盐酸 、 硫酸 、 sodium hydride 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 23.75h， 生成 3,5-diacetyl aniline
  参考文献：
  名称：

  Deoxyhypusine Synthase Inhibitor CNI-1493 的接头区域修饰衍生物抑制 HIV-1 复制

  摘要：

  抑制参与病毒复制的细胞因子可能是常用的靶向病毒酶策略的重要替代方案。脒腙 CNI-1493 是一种有效的脱氧黄嘌呤合酶 (DHS) 抑制剂，可阻止细胞因子 eIF-5A 的激活，从而抑制 HIV 复制和许多其他疾病。在这里，我们报告了一系列 CNI-1493 类似物的设计、合成和生物学评价。CNI-1493 中的癸二酰基接头被不同的烷基或芳基二羧酸取代。大多数测试的衍生物以剂量依赖性方式有效抑制 HIV-1 复制，而没有显示出毒副作用。刚性衍生物的意外抗病毒活性指向了先前对 CNI-1493 假设的第二种结合模式。而且，分析了 CNI-1493 的化学稳定性，显示出亚氨基键的连续水解。通过分子动力学模拟，研究了母体 CNI-1493 在溶液中的行为及其与 DHS 的相互作用。

  DOI：

  10.1002/ardp.201500323

文献信息

• Pyrimidine Derivatives
  申请人：Klebl Bert

  公开号：US20080187575A1

  公开（公告）日：2008-08-07

  The present invention relates to pyrimidine derivatives, methods for their synthesis, and the use of said pyrimidine derivatives as pharmaceutically active agents, especially for the prophylaxis and/or treatment of cell proliferation disorders, cancer, leukemia, erectile dysfunction, cardiovascular diseases and disorders, inflammatory diseases, transplant rejection, immunological diseases, neuroimmunological diseases, autoimmune diseases, infective diseases including opportunistic infections, prion diseases and/or neuro-degeneration. Furthermore, the present invention relates to pharmaceutical compositions containing at least one pyrimidine derivative and/or pharmaceutically acceptable salts thereof as an active ingredient together with at least one pharmaceutically acceptable carrier, excipient or diluents as well as to methods for prophylaxis and/or treatment of the above-mentioned diseases and disorders.

  本发明涉及嘧啶衍生物，其合成方法，以及所述嘧啶衍生物作为药用活性剂的用途，特别是用于预防和/或治疗细胞增殖紊乱、癌症、白血病、勃起功能障碍、心血管疾病和紊乱、炎症性疾病、移植排斥、免疫性疾病、神经免疫性疾病、自身免疫性疾病、感染性疾病包括机会性感染、朊病和/或神经退行性疾病。此外，本发明涉及含有至少一种嘧啶衍生物和/或其药用可接受盐作为活性成分的药物组合物，以及用于预防和/或治疗上述疾病和紊乱的方法。
• Guanylhydrazones and their use to treat inflammatory conditions
  申请人：The Picower Institute for Medical Research

  公开号：US05750573A1

  公开（公告）日：1998-05-12

  This invention concerns new methods and compositions that are useful in preventing and ameliorating cachexia, the clinical syndrome of poor nutritional status and bodily wasting associated with cancer and other chronic diseases. More particularly, the invention relates to aromatic guanylhydrazone (more properly termed amidinohydrazone) compositions and their use to inhibit the uptake of arginine by macrophages and/or its conversion to urea. These compositions and methods are also useful in preventing the generation of nitric oxide (NO) by cells, and so to prevent NO-mediated inflammation and other responses in persons in need of same. In another embodiment, the compounds can be used to inhibit arginine uptake in arginine-dependent tumors and infections.

  这项发明涉及新的方法和组合物，可用于预防和改善消瘦症，即与癌症和其他慢性疾病相关的营养状况不佳和身体消耗的临床综合征。更具体地，该发明涉及芳香基胍基脲（更确切地称为胍基脲）组合物及其用于抑制巨噬细胞对精氨酸的摄取和/或其转化为尿素。这些组合物和方法还可用于预防细胞产生一氧化氮（NO），从而预防需要相同的人体内的NO介导的炎症和其他反应。在另一实施例中，这些化合物可用于抑制精氨酸依赖性肿瘤和感染中的精氨酸摄取。
• From rigid cyclic templates to conformationally stabilized acyclic scaffolds. Part I: The discovery of CCR3 antagonist development candidate BMS-639623 with picomolar inhibition potency against eosinophil chemotaxis
  作者：Joseph B. Santella、Daniel S. Gardner、Wenqing Yao、Chongsheng Shi、Prabhakar Reddy、Andrew J. Tebben、George V. DeLucca、Dean A. Wacker、Paul S. Watson、Patricia K. Welch、Eric A. Wadman、Paul Davies、Kimberly A. Solomon、Dani M. Graden、Swamy Yeleswaram、Sandhya Mandlekar、Ilona Kariv、Carl P. Decicco、Soo S. Ko、Percy H. Carter、John V. Duncia

  DOI：10.1016/j.bmcl.2007.11.067

  日期：2008.1

  Conformational analysis of trans-1,2-disubstituted cyclohexane CCR3 antagonist 2 revealed that the cyclohexane linker could be replaced by an acyclic syn-alpha-methyl-beta-hydroxypropyl linker. Synthesis and biological evaluation of mono- and disubstituted propyl linkers support this conformational correlation. It was also found that the alpha-methyl group to the urea lowered protein binding and that

  反式1,2-二取代的环己烷CCR3拮抗剂2的构象分析表明，环己烷接头可被无环的顺式α-甲基-β-羟丙基接头取代。单取代和双取代丙基连接基的合成和生物学评估支持这种构象相关性。还发现与尿素的α-甲基降低了蛋白结合，而β-羟基降低了对CYP2D6的亲和力。从头算计算表明，α-甲基基团控制着分子内三个关键功能的空间取向。具有嗜酸性粒细胞趋化性IC（50）= 38 pM的α-甲基-β-羟丙基尿素31被选择进入临床治疗哮喘的研究。
• Pyrimidinium-guanidiniminoethylphenyl-guanidinoalkyl-amines and guanidiniminoethylphenyl-guanidinoalkylamines as pharmaceutically active new substances
  申请人：Mondobiotech SA

  公开号：EP1413300A1

  公开（公告）日：2004-04-28

  The present invention relates to new compositions and methods for use as pharmaceutically active agents, especially for prophylaxis and prevention in virally caused infections and diseases, tumor necrosis factor alpha (TNFα)-related inflammatory conditions and diseases, graft rejection after organ or tissue transplantations, and cancer. The innovative compounds are inhibitors of Hypusine formation and nuclear transport of distinct RNAs from nucleus to cytoplasm.

  本发明涉及新的组合物和方法，用作药物活性剂，特别是用于预防和治疗病毒引起的感染和疾病、肿瘤坏死因子α（TNFα）相关的炎症性疾病、器官或组织移植后的移植排斥反应以及癌症。这些创新化合物是Hypusine形成和将特定RNA从细胞核转运到细胞质的抑制剂。
• Behavior of organic compounds confined in monoliths of sol–gel silica glass. Effects of guest–host hydrogen bonding on uptake, release, and isomerization of the guest compounds
  作者：Jovica D. Badjić、Nenad M. Kostić

  DOI：10.1039/b005823h

  日期：——

  Various proteins, catalysts, and other compounds can be encapsulated or diffused into porous sol–gel glasses, but little is known about their interactions with the glass matrix. We report unexpectedly large effects that hydrogen bonding between organic compounds and sol–gel silica has on equilibria and reactions involving these guest compounds. Silica monolith immersed in a solution takes up the organic solute. Styrene, which is incapable of hydrogen bonding, becomes evenly distributed between external solution and the glass. Aniline and N,N-diethyl-p-methoxybenzamide, which are capable of hydrogen bonding, become extracted into the glass when the solvent (neat CCl4) does not interfere with their hydrogen bonding with silica. They become evenly distributed between the solution and the glass when a component of the solvent (DMF added to CCl4) or chemical modification (trimethylsilylation) of the silica surface suppresses hydrogen bonding of the guests with the surface. Ultraviolet spectra show that silica–guest interactions are present when the guest uptake is excessive and absent when this uptake is balanced. Ultraviolet spectra of aniline show that the hydrogen atoms are donated by silica to the guest. Not only the extent, but also the rate, of uptake is enhanced when the guest makes hydrogen bonds to the silica matrix; suppression of these bonds lowers the uptake rate. Silica monolith extracts trans-3,3′-diacetylazobenzene from a CCl4 solution 1250-fold. Upon addition of DMF, hydrogen bonds are broken, and the monolith completely releases the solute into the external solution. Five derivatives of azobenzene (3,3′-dimethyl-, 3-acetyl-, 3,3′-diacetyl-, 3,5-diacetyl-, and 3,3′,5,5′-tetraacetylazobenzene), which differ in the propensity for accepting hydrogen atoms, served as photochromic probes and showed the effect of hydrogen bonding on reactivity. Both the photoinduced (trans-to-cis) and the subsequent thermal (cis-to-trans) isomerizations of the five derivatives obey the first-order law in glass as well as in free solution. When the solvent (neat CCl4) allows hydrogen bonding, the proportion of the isomers in the photostationary state differs between the glass and solution, and the rate constant for the thermal reaction is two to four times (in different derivatives) smaller in the glass than in solution. Evidently, hydrogen bonding retards the rearrangement of the probe molecules in the silica matrix. When hydrogen bonding is abolished (by addition of DMF to CCl4), the compositions of the photostationary state in the glass and in solution become equal, and so do the rate constants. Effects of hydrogen bonding on enzymes encapsulated in sol–gel glass and on the distribution of analytes between the glass monolith and the sample solution should be taken into consideration when designing accurate biosensors.

  各种蛋白质、催化剂和其他化合物都可以封装或扩散到多孔溶胶玻璃中，但人们对它们与玻璃基质的相互作用却知之甚少。我们报告了有机化合物与溶胶二氧化硅之间的氢键作用对涉及这些客体化合物的平衡和反应产生的意想不到的巨大影响。浸入溶液中的二氧化硅整体吸收有机溶质。不能发生氢键作用的苯乙烯会均匀地分布在外部溶液和玻璃之间。苯胺和 N,N-二乙基对甲氧基苯甲酰胺能够形成氢键，当溶剂（纯净的 CCl4）不干扰它们与二氧化硅的氢键结合时，它们就会被萃取到玻璃中。当溶剂中的某种成分（在 CCl4 中加入 DMF）或二氧化硅表面的化学修饰（三甲基硅烷化）抑制了客体与二氧化硅表面的氢键结合时，它们就会在溶液和玻璃之间均匀分布。紫外光谱显示，当客体吸收过多时，二氧化硅与客体之间存在相互作用，而当这种吸收平衡时，则不存在相互作用。苯胺的紫外光谱显示，二氧化硅向客体提供了氢原子。当客体与二氧化硅基质形成氢键时，吸收的程度和速度都会提高；抑制这些氢键则会降低吸收速度。二氧化硅整体从 CCl4 溶液中萃取反式-3,3â²-二乙酰偶氮苯的能力提高了 1250 倍。加入 DMF 后，氢键断裂，硅石将溶质完全释放到外部溶液中。偶氮苯的五种衍生物（3,3â²-二甲基偶氮苯、3-乙酰基偶氮苯、3,3â²-二乙酰基偶氮苯、3,5-二乙酰基偶氮苯和 3,3â²,5,5â²-四乙酰基偶氮苯）接受氢原子的倾向各不相同，它们可用作光致变色探针，并显示了氢键对反应活性的影响。这五种衍生物的光诱导异构化（反式-顺式）和随后的热异构化（顺式-反式）在玻璃中和自由溶液中都符合一阶定律。当溶剂（纯净的 CCl4）允许氢键作用时，玻璃和溶液中处于光静止状态的异构体比例不同，热反应的速率常数在玻璃中比在溶液中小 2 到 4 倍（对于不同的衍生物）。显然，氢键阻碍了探针分子在二氧化硅基质中的重新排列。当氢键被取消时（在 CCl4 中加入 DMF），玻璃中的光静止态成分与溶液中的光静止态成分相等，速率常数也相等。在设计精确的生物传感器时，应考虑到氢键对封装在溶胶玻璃中的酶以及分析物在玻璃整体和样品溶液之间分布的影响。