6-allylaminouracil | 72255-74-4

• 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: 6-allylaminouracil
• 英文别名: 6-(prop-2-enylamino)-1H-pyrimidine-2,4-dione
• CAS: 72255-74-4
• 化学式: C₇H₉N₃O₂
• 分子量: 167.167
• InChiKey: JEBCEODODJJXLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-allylaminouracil 在 苯膦酰二氯 、 盐酸 、 sodium dithionite 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 33.67h， 生成 1-[3-Prop-2-enyl-7-(prop-2-enylamino)triazolo[4,5-d]pyrimidin-5-yl]piperidin-4-one
  参考文献：
  名称：

  New Purines and Purine Analogs as Modulators of Multidrug Resistance

  摘要：

  A series of 36 purine and purine analog derivatives have been synthesized and tested for their ability to modulate multidrug resistance in vitro (P388/VCR-20 and KB-A1 cells) and in vivo (P388/VCR leukemia). Compounds were compared to S9788, a triazine derivative which has already shown some activity during phase 1 clinical trials and also a limiting cardiovascular side effect possibly linked to its calcium channel affinity. The fact that active compounds increase adriamycin accumulation in the resistant KB-A1 cells, and not in the sensitive KB-3-1 cells, suggests they act predominantly by inhibiting the P-glycoprotein-catalyzed efflux of cytotoxic agents. No direct relation was found between the affinity for the phenylalkylamine binding site of the calcium channel and in vitro sensitization of resistant cells. In vivo, when administered po in association with vincristine (0.25 mg/kg), five compounds (3, 4, 9, 25, and 26), of very differing calcium channel affinities (K-i from 5 to 560 nM), fully restored (T/V greater than or equal to 1.4) the sensitivity of P388/VCR leukemia to vincristine.

  DOI：

  10.1021/jm960361i
• 作为产物：
  描述：

  6-氯尿嘧啶 、 丙烯胺 以 二乙二醇二甲醚 为溶剂， 以80%的产率得到6-allylaminouracil
  参考文献：
  名称：

  枯草芽孢杆菌DNA聚合酶III的抑制剂。6-茴香尿嘧啶和6-（烷基氨基）尿嘧啶。

  摘要：

  发现取代的6-茴香胺嘧啶是来自枯草芽孢杆菌的复制特异性酶DNA聚合酶III的有效抑制剂。通过在苯环的间位和对位包含小烷基或卤素，可以最大程度地发挥抑制作用。极性取代基大大降低了活性。定性结构-活性关系表明，该元位置可以耐受较大的基团，这表明该位置可能适合引入能够不可逆地结合酶的基团。几种6-（烷基氨基）尿嘧啶是DNA聚合酶III的弱抑制剂。用于酶结合的最佳烷基是正戊基和正己基，它们显然可以占据平面酶结合位点。6-苯胺嘧啶对突变型DNA聚合酶的各种活性，

  DOI：

  10.1021/jm00175a007

文献信息

• Inhibitors of Bacillus subtilis DNA polymerase III. 6-Anilinouracils and 6-(alkylamino)uracils
  作者：George E. Wright、Neal C. Brown

  DOI：10.1021/jm00175a007

  日期：1980.1

  irreversibly binding to the enzyme. Several 6-(alkylamino)uracils were weak inhibitors of DNA polymerases III; the optimum alkyl groups for enzyme binding were n-pentyl and n-hexyl, which apparently can occupy the planar enzyme binding site. The varied activities of 6-anilinouracils on a mutant DNA polymerase, resistant to 6-(phenylhydrazino)- and 6-(benzylamino)uracils bearing a p-OH or NH2 group, have altered

  发现取代的6-茴香胺嘧啶是来自枯草芽孢杆菌的复制特异性酶DNA聚合酶III的有效抑制剂。通过在苯环的间位和对位包含小烷基或卤素，可以最大程度地发挥抑制作用。极性取代基大大降低了活性。定性结构-活性关系表明，该元位置可以耐受较大的基团，这表明该位置可能适合引入能够不可逆地结合酶的基团。几种6-（烷基氨基）尿嘧啶是DNA聚合酶III的弱抑制剂。用于酶结合的最佳烷基是正戊基和正己基，它们显然可以占据平面酶结合位点。6-苯胺嘧啶对突变型DNA聚合酶的各种活性，
• Immunosuppressive effects of 8-substituted xanthine derivatives
  申请人：K.U. Leuven Research & Development

  公开号：EP0956855A1

  公开（公告）日：1999-11-17

  The invention relates to a novel use of 8 substituted xanthine derivatives for the manufacture of a medicament for the treatment of auto-immuno disorders. The invention relates in particular to the use of a xanthine derivative of general formula (I): wherein: R1, R2 and R3 are independently hydrogen, saturated or unsaturated aliphatic chains which may be straight or branched having 1 to 6 carbon atoms; X and Y are independently oxygen or sulfur; Z1 is selected from the group comprising a thienyl; furanyl; cyclopentyl, phenyl or a substituted by Z2 or unsubstituted phenyl; wherein Z2 is selected from the group comprising phenyl; sulfonic acid; unsubstituted or N-substituted sulfonamide with substituents such as alkyl, aminoalkyl where the amino group may be substituted itself with lower alkyl groups bearing 1 to 4 carbon atoms; nitro; halogen substituted or unsubstituted amino group; aliphatic chain with 1 to 3 carbon atoms; halogenated aliphatic chain with 1 to 3 carbon atoms; aliphatic chain containing ether functions, acids, esters, amides, substituted or unsubstituted amines having 1 to 3 carbon atoms, nitro, sulfonamides or a combination of these functional groups with a maximum length of the chain of 12 atoms, or a pharmaceutically acceptable salt thereof for the manufacture of a medicament for the treatment of auto-immuno disorders.

  本发明涉及一种 8 取代黄嘌呤衍生物用于制造治疗自身免疫疾病药物的新用途。 本发明尤其涉及通式（I）的黄嘌呤衍生物的用途： 其中 R1、R2 和 R3 独立地是氢、饱和或不饱和脂肪族链，可以是直链或支链，具有 1 至 6 个碳原子； X 和 Y 独立地为氧或硫； Z1 选自包括噻吩基、呋喃基、环戊基、苯基或被 Z2 取代或未取代的苯基；其中 Z2 选自包括苯基、磺酸、未取代或 N-取代的磺酰胺，其取代基包括烷基、氨基烷基（其中氨基本身可被含 1 至 4 个碳原子的低级烷基取代）、硝基、卤素取代或未取代的氨基烷基、呋喃基、环戊基、苯基或被 Z2 取代或未取代的苯基；卤素取代或未取代的氨基；具有 1 至 3 个碳原子的脂肪族链；具有 1 至 3 个碳原子的卤代脂肪族链；含有醚官能团的脂肪族链、酸、酯、酰胺、具有 1 至 3 个碳原子的取代或未取代的胺、硝基、磺酰胺或这些官能团的组合，链的最大长度为 12 个原子、 或其药学上可接受的盐，用于制造治疗自身免疫性疾病的药物。
• Immunosuppressive effects of 8 substituted xanthine derivatives
  申请人：K.U. Leuven Research & Development

  公开号：EP0956855B1

  公开（公告）日：2003-03-12
• HIGHLY SOLUBLE PYRIMIDO-DIONE-QUINOLINE COMPOUNDS AND THEIR USE IN THE TREATMENT OF CANCER
  申请人：Weissman Allan

  公开号：US20100056549A1

  公开（公告）日：2010-03-04

  The present invention features pyrimido-dione-quinoline compounds having improved solubility, pharmaceutical compositions of substituted pyrimido-dione-quinoline compounds and methods of treating a patient suffering from cancer, the method comprising administering to a patient one or more pyrimido-dione-quinoline compounds of the invention.
• US6177437B1
  申请人：——

  公开号：US6177437B1

  公开（公告）日：2001-01-23