5-decylbarbituric acid | 101098-70-8

• 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: 5-decylbarbituric acid
• 英文别名: 5-decyl-barbituric acid；5-Decyl-barbitursaeure；5-decyl-1,3-diazinane-2,4,6-trione
• CAS: 101098-70-8
• 化学式: C₁₄H₂₄N₂O₃
• 分子量: 268.356
• InChiKey: NUEVOKYGRAPXGJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  75.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-decylbarbituric acid 在 氢溴酸 、 溴 作用下， 以 水 为溶剂， 生成 5-bromo-5-decylbarbituric acid
  参考文献：
  名称：

  US6110924

  摘要：

  公开号：
• 作为产物：
  描述：

  正癸基丙二酸二乙酯 在 sodium ethanolate 、 尿素 作用下， 以 乙醇 、 水 为溶剂， 生成 5-decylbarbituric acid
  参考文献：
  名称：

  US6110924

  摘要：

  公开号：

文献信息

• Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates
  作者：Branko S. Jursic、Edwin D. Stevens

  DOI：10.1016/s0040-4039(03)00111-4

  日期：2003.3

  Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate

  通过系统地研究反应条件，开发了用于获得大量取代的5-烷基和5-苄基巴比妥酸的非常有效的制备方法。该过程包括两步准备，其中第二步是还原锌粉/酸。对于制备5-烷基巴比妥酸酯，第一步是制备5-酰基或5-亚烷基巴比妥酸酯。如果5-苄基巴比妥酸酯是目标产物，则第一步包括制备5-亚苄基。无论第一步的性质如何，所有反应的合成产率均约为90％，而分离和纯化仅涉及结晶。
• Barbituric acid derivatives with antimetastatic and antitumor activity
  申请人：Roche Diagnostics GmbH

  公开号：US06335332B1

  公开（公告）日：2002-01-01

  The invention is directed to barbituric acid derivatives having inhibitory activity for matrix maetalloproteases comprised of formula (I): pharmaceutical compositions thereof, processes for preparing the derivatives, and methods for treating diseases associated with elevated or uncontrolled levels of matrix metalloprotease activity, e.g., cancer, specifically tumor progression and tumor metastasis, inflammation, or as a method of contraception.

  该发明涉及具有抑制基质金属蛋白酶活性的巴比妥酸衍生物，其化学式为(I)：其药物组合物、制备衍生物的方法以及治疗与基质金属蛋白酶活性升高或失控相关的疾病的方法，例如癌症、特别是肿瘤进展和肿瘤转移、炎症，或作为避孕方法。
• Multiple hydrogen bonded mesomorphic complexes between complementary 1,3,5-triazine and pyrimidine derivatives
  作者：Alexandra Kohlmeier、Laura Vogel、Dietmar Janietz

  DOI：10.1039/c3sm51554k

  日期：——

  A 2,4-diamino-6-phenyl-1,3,5-triazine grafted with two semiperfluorinated chains at the phenyl substituent has been investigated in binary mixtures with complementary orotic acid and barbituric acid derivatives carrying either a lipophilic alkyl or a semiperfluoroalkyl tail. Equimolar mixtures of the triazine with nucleobases form triple hydrogen-bonded heterodimers with an elongated central core. Mesomorphic properties are observed only if the pyrimidinone component provides an additional free NH function not involved in triple H-bonding with the triazine nucleus. In that case, additional H-bond interactions orthogonal to the rod-shaped core of the heterodimers initiate the formation of cyclotrimeric rosette-type associates with circular geometry of the polar core region. Rosettes of heterodimers involving an alkyl substituted nucleobase organize to hexagonal columnar mesophases. Replacing the alkyl tail of the pyrimidine with a semiperfluorinated fragment leads to the formation of a micellar cubic phase. The individual micelles are composed of segmented columns three-dimensionally surrounded by a continuum of the semiperfluorinated segments.

  我们研究了在苯基取代基上接枝了两条半哌氟化链的 2,4-二氨基-6-苯基-1,3,5-三嗪与带有亲脂烷基或半哌氟烷基尾部的互补奥罗酸和巴比妥酸衍生物的二元混合物。三嗪与核碱基的等摩尔混合物会形成三重氢键异二聚体，并具有一个拉长的中心核。只有当嘧啶酮成分提供了额外的自由 NH 功能而不参与与三嗪核的三重氢键结合时，才会观察到介形特性。在这种情况下，与异源二聚体的杆状核心正交的额外 H 键相互作用会启动环状三聚体莲座型结合体的形成，其极性核心区域呈环状几何形状。有烷基取代的核碱基参与的杂二聚体的玫瑰花环组织成六角柱状介相。用半哌氟化片段取代嘧啶的烷基尾部可形成立方胶束相。单个胶束由三维分段柱组成，周围环绕着半哌氟化片段的连续体。
• Barbituric acid derivatives, processes for their production and pharmaceutical agents containing these compounds
  申请人：Roche Diagnostics GmbH

  公开号：US06472396B1

  公开（公告）日：2002-10-29

  Compounds of formula I, useful as matrix metalloprotease inhibitors, wherein X, Y and Z are each oxygen; R1 is selected from the group consisting of (a) n-octyl, (b) n-decyl, (c) biphenyl and (d) (4-phenoxy)phenyl, wherein the terminal monocycle for moieties (c)-(d) is unsubstituted or substituted by a substituent selected from the group consisting of —NH2, —NO2, —SO2NH2, —SO2CH3, acetyl, hydroxy, methoxy, ethoxy, cyano and halogen; R2 and R3 are each hydrogen; and R4 and R5, together with the nitrogen atom to which they are bound, form a piperazinyl or piperidyl ring, wherein the piperazinyl ring is substituted in the 4-position with a substituent selected from the group consisting of (a) a 6-membered aromatic monocycle having 0, 1 or 2 nitrogen atoms and the remainder of the atoms in the monocycle being carbon and (b) hydroxy-C1-C6 alkyl, wherein the monocycle is unsubstituted or substituted by a substituent selected from the group consisting of halogen, —NH2, —NO2, —SO2NH2, —SO2CH3, acetyl and cyano.

  化合物I的式子，可用作基质金属蛋白酶抑制剂，其中X、Y和Z均为氧；R1选自（a）正辛基，（b）正癸基，（c）联苯基和（d）（4-苯氧基）苯基，其中对于基团（c）-（d）的末端单环可以是未取代的或取代的，所取代基团选自—NH2，—NO2，—SO2NH2，—SO2CH3，乙酰基，羟基，甲氧基，乙氧基，氰基和卤素；R2和R3均为氢；R4和R5与它们所连接的氮原子一起形成哌嗪基或哌啶基环，其中哌嗪基环在4位上被选自以下基团的取代基所取代：（a）具有0、1或2个氮原子和单环中其余原子为碳的6-成员芳香单环和（b）羟基-C1-C6烷基，其中单环未取代或被选自卤素，—NH2，— ，—SO2NH2，—SO2CH3，乙酰基和氰基的取代基所取代。
• Oda et al., Bulletin of the Institute for Chemical Research, Kyoto University, 1953, vol. 31, p. 61
  作者：Oda et al.

  DOI：——

  日期：——