1-cyclohexylpyrimidine-2,4,6(1H,3H,5H)-trione | 1015-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-cyclohexylpyrimidine-2,4,6(1H,3H,5H)-trione
• 英文别名: 1-Cyclohexylbarbituric acid；1-cyclohexyl-pyrimidine-2,4,6-trione；1-cyclohexylpyrimidinetrione；1-Cyclohexylperhydropyrimidin-2,4,6-trion；1-Cyclohexyl-barbitursaeure；N-Cyclohexylbarbitursaeure；1-cyclohexyl-1,3-diazinane-2,4,6-trione
• CAS: 1015-65-2
• 化学式: C₁₀H₁₄N₂O₃
• mdl: MFCD01217006
• 分子量: 210.233
• InChiKey: ZTUIKEVPLFQEJR-UHFFFAOYSA-N

物化性质

• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933540000

反应信息

• 作为反应物：
  描述：

  1-cyclohexylpyrimidine-2,4,6(1H,3H,5H)-trione 在 sodium hydroxide 、 水 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 异丁酰胺 为溶剂， 反应 6.0h， 生成 N-[(1-cyclohexyl-6-hydroxy-3-{[4-(1-methylethyl)phenyl]methyl}-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)carbonyl]glycine
  参考文献：
  名称：

  [EN] PROLYL HYDROXYLASE INHIBITORS
  [FR] INHIBITEURS DE PROLYLE HYDROXYLASE

  摘要：

  公开号：

  WO2007150011A3
• 作为产物：
  描述：

  N-环己基脲 、 丙二酸二乙酯 生成 1-cyclohexylpyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  Singh, Palwinder; Paul, Kamaldeep, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 5, p. 1105 - 1108

  摘要：

  DOI：

文献信息

• Antineoplastika, 14. Mitt.1) Cyclohexylderivate der 5-aminomethinylierten Barbitursäure
  作者：Alfred Kreutzberger、Elfriede Kreutzberger

  DOI：10.1002/ardp.19833160104

  日期：——

  Aus der mit s‐Triazin (1) durchführbaren Aminomethinylierung der 1‐Cyclohexyl‐ (2a) und 1,3‐Dicyclohexylbarbitursäure (2b) gehen die korrespondierenden Cyclohexylderivate der 5‐aminomethinylierten Barbitursäure 4a und 4b hervor. Insbesondere 4b vermag antineoplastische Effekte auszulösen.

  1-环己基- (2a) 和 1,3- 二环己基巴比妥酸 (2b) 的氨基甲炔化反应可以用 s-三嗪 (1) 进行，产生相应的 5-氨基甲炔基化巴比妥酸 4a 和 4b 的环己基衍生物. 4b 特别是能够触发抗肿瘤作用。
• Synthesis of Pyrimidine Derivatives Possessing an Antioxidative Property and Their Inhibitory Effects on Picryl Chloride-Induced Contact Hypersensitivity Reaction
  作者：Yoshiaki Isobe、Kosaku Hirota

  DOI：10.1248/cpb.51.1451

  日期：——

  We conducted a preliminary structure–activity relationship (SAR) study of some barbituric acid and uracil derivatives against the picryl chloride-induced contact hypersensitivity reaction. The introduction of an antioxidative moiety to the side chain of the C(6)-position of uracil was effective against this model. The introduction of dimethoxyphenol (8b) or dimethylphenol (8c) instead of di-t-butylphenol (8a) as an antioxidative moiety gave diminished activities, so, the reactive oxygen would contribute to the inflammation of this model, and an antioxidative activity was required for exhibiting the inhibitory activity. The inhibitory activity was significantly affected by the substituent at the N(1)-phenyl moiety.

  我们对一些巴比妥酸和尿嘧啶衍生物针对苦基氯引起的接触超敏反应进行了初步构效关系（SAR）研究。在尿嘧啶的 C(6) 位侧链上引入抗氧化部分可有效对抗该模型。引入二甲氧基苯酚（8b）或二甲基苯酚（8c）代替二叔丁基苯酚（8a）作为抗氧化部分会降低活性，因此，活性氧会导致该模型的炎症，因此需要抗氧化活性用于表现出抑制活性。 N(1)-苯基部分的取代基显着影响抑制活性。
• Pyrimidine derivatives, method for preparation thereof and pharmaceutical composition having said derivatives as active elements
  申请人：JAPAN ENERGY CORPORATION

  公开号：EP0546661A1

  公开（公告）日：1993-06-16

  The invention provides i) pyrimidine derivatives of the following formula (I), their pharmaceutically acceptable salt and method for preparation thereof. (R₁ and R₂ represent independently hydrogen atom, linear or branched alkyl group, substituted or non-substituted phenyl or cyclohexyl group; and R₃ represents linear or branched lower alkyl or alkoxy group; represents both stereo isomers.); and ii) Pharmaceutical compositions having the pyrimidine derivatives of formula (I) or pharmaceutically acceptable salts thereof, particularly anti-inflammatory agents, agents for treating respiratory tract disorders or agents for treating cerebrovascular diseases.

  本发明提供了以下式(I)的嘧啶衍生物，其药学上可接受的盐和制备方法。(其中，R₁和R₂分别表示氢原子、线性或支链烷基、取代或未取代的苯基或环己基；R₃表示线性或支链低级烷基或烷氧基；代表两个立体异构体。);以及具有式(I)的嘧啶衍生物或其药学上可接受的盐的制剂，特别是用于治疗炎症、呼吸道疾病或脑血管疾病的药物。
• TETRACYCLICAL DERIVATIVES FROM PYRIMIDINE
  申请人：Ashkinazi, Rimma Iliinichna

  公开号：EP1022278A1

  公开（公告）日：2000-07-26

  Biologically active substance on the basis of tetracyclic nitrogen heterocycles of pyrimidine series (applicant - inventors R.I. Ashkinazi and K.A. Krasnov). The present invention relates to medicine, and more specifically to pharmacology, veterinary cosmetology, and in particular to synthetic biologically active compounds of a heterocycle series, which possess antimicrobial, antiviral, antichlamydia and immune stimulating activities: derivatives of 5-oxo-5H-[1]-benzopyrano-[5,6-b]-4-oxo-4H-[1,2]-pyrimido-1,4,5,64-tetrahydro-1,3-thiazine. The compounds are provided mainly for treating tuberculosis, mycobacteriosis, viral diseases, infections caused by chlamydias, and diseases which are accompanied by immunodeficiency, particularly malignant neoplasm. In addition, the above mentioned compounds can be used for the same purposes in veterinary medicine and cosmetology. An objective of the invention is to obtain new chemical compounds which have high antimicrobial activity, particularly with respect to strains of mycobacteria that are resistant to isoniazid, which is standardly used to treat mycobacteria. Compounds of the invention simultaneously possess antiviral activity (relative to herpes simplex viruses), antichlamydial activity, and also stimulate production of endogenic interferons in organisms. In other words, the objective of the invention is a chemical synthesis of biologically active substances which are superior to the prototype not only in a range of action on strains of tuberculosis and other mycobacteria, but also possess antiviral, antichylamidial and immuno stimulating action. The objective is solved by synthesis of new class of heterocyclic compounds-derivatives of 5-oxo-5H-[1]-benzopyrano[5,6-b]-4-oxo-4H-[1,2]-pyrimido-1,4,5,6-tetrahydro-1,3-thiazine (1) of general formula (1).    (I-X),where: R1 = H or a halogen; R2 = H, halogen, nitro, hydroxy, or methoxy. The objective can be solved with R1 = R2 = H (I); R1 = H and R2 = Cl (II); R1 = R2 = Cl (III); R1 = H and R2 = Br (IV); R1 = R2 = Br (V); R1 = H and R2 = NO2 (VI); R1 = Cl and R2 = NO2 (VIIl); R1 = Cl and R2 = NO2 (VII); R1 = Br and R2 = NO2 (VIII); R1 = H and R2 = OCH3 (IX); R1 = H and R2 = OH (X). The proposed synthesis of the claimed compounds includes two main stages: 1. 4-oxo-4H-6-oxy-[1,2-d]-pyrimido-1, 4, 5, 6-tetrahydro-1,3-thiazine(XI) is synthesized from 2-thiobarbituric acid (XII) and 1,3-dihalogenopropane(XIII); and 2. A target compound (I-X) is produced from the intermediate substance (XI) obtained in the first stage and corresponding derivative of salicylaldehyde (XIV). The method is common for all members of the group. The subject matter of the present invention it explained by two examples of synthesis of the intermediate substance and three examples of synthesis of claimed substances, two tables of yield of intermediate and target products, two tables of characteristics of target products, and data of seven experiments for determination of their biological properties.

  基于嘧啶系列四环氮杂环的生物活性物质（申请人-发明人 R.I. Ashkinazi 和 K.A. Krasnov）。本发明涉及医学，更具体地说，涉及药理学、兽医美容学，尤其涉及具有抗菌、抗病毒、抗衣原体和免疫刺激活性的杂环系列合成生物活性化合物：5-氧代-5H-[1]-苯并吡喃-[5,6-b]-4-氧代-4H-[1,2]-嘧啶-1,4,5,64-四氢-1,3-噻嗪的衍生物。这些化合物主要用于治疗结核病、分枝杆菌病、病毒性疾病、由衣原体引起的感染以及伴有免疫缺陷的疾病，尤其是恶性肿瘤。此外，上述化合物还可用于兽医和美容领域。 本发明的一个目的是获得具有高抗菌活性的新化合物，特别是对异烟肼（治疗分枝杆菌的标准药物）具有抗药性的分枝杆菌菌株。本发明的化合物同时具有抗病毒活性（相对于单纯疱疹病毒）和抗衣原体活性，还能刺激生物体产生内源性干扰素。换句话说，本发明的目的是用化学方法合成生物活性物质，这些物质不仅在对结核菌和其他分枝杆菌的作用范围上优于原型物质，而且还具有抗病毒、抗衣原体和免疫刺激作用。 为了实现这一目标，我们合成了通式（1）为 5-氧代-5H-[1]-苯并吡喃并[5,6-b]-4-氧代-4H-[1,2]-嘧啶-1,4,5,6-四氢-1,3-噻嗪（1）的新型杂环化合物-衍生物。 (I-X)，其中R1 = H 或卤素；R2 = H、卤素、硝基、羟基或甲氧基。 目标可以用 R1 = R2 = H (I)；R1 = H 和 R2 = Cl (II)；R1 = R2 = Cl (III)；R1 = H 和 R2 = Br (IV)；R1 = R2 = Br (V)；R1 = H 和 R2 = NO2 (VI)；R1 = Cl 和 R2 = NO2 (VIIl)；R1 = Cl 和 R2 = NO2 (VII)；R1 = Br 和 R2 = NO2 (VIII)；R1 = H 和 R2 = OCH3 (IX)；R1 = H 和 R2 = OH (X)来解决。 拟议的权利要求化合物的合成包括两个主要阶段： 1.4-oxo-4H-6-oxy-[1,2-d]-pyrimido-1, 4, 5, 6-tetrahydro-1,3-thiazine(XI) 由 2-thiobarbituric acid (XII) 和 1,3-dihalogenopropane(XIII) 合成；以及 2.由第一阶段得到的中间物质（XI）和相应的水杨醛衍生物（XIV）制得目标化合物（I-X）。该方法适用于该组的所有成员。 本发明的主题通过两个中间物质合成实例和三个权利要求物质合成实例、两个中间产物和目标产物产率表、两个目标产物特性表以及七个测定其生物特性的实验数据来说明。
• ——
  作者：K. A. Krasnov、V. G. Kartsev、E. E. Santarovich

  DOI：10.1023/a:1019973404301

  日期：——