2-氨基-6-(乙基氨基)-4(1H)-嘧啶酮 | 164525-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-氨基-6-(乙基氨基)-4(1H)-嘧啶酮
• 中文别名: 2-氨基-6-(乙氨基)嘧啶-4(3H)-酮；2-氨基-6-(乙氨基)嘧啶-4(3h)-酮
• 英文名称: 2-amino-6-ethylaminopyrimidin-4(3H)-one
• 英文别名: 6-ethylamino-2-amino-3H-pyrimidin-4-one；6-Aethylamino-2-amino-3H-pyrimidin-4-on；2-Amino-6-(ethylamino)pyrimidin-4(3H)-one；2-amino-4-(ethylamino)-1H-pyrimidin-6-one
• CAS: 164525-11-5
• 化学式: C₆H₁₀N₄O
• 分子量: 154.172
• InChiKey: OYJHYDNQKBXDFD-UHFFFAOYSA-N

物化性质

• 熔点：
  229-230 °C
• 沸点：
  304.0±45.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-6-(乙基氨基)-4(1H)-嘧啶酮 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以13%的产率得到2-amino-4-(ethylamino)-5-nitroso-1H-pyrimidin-6-one
  参考文献：
  名称：

  单环蝶啶类似物。6-氨基-5-亚硝基异胞嘧啶对大肠杆菌二氢蝶呤合酶的抑制作用。

  摘要：

  在体外评价了多种5，6-二取代的异胞嘧啶衍生物作为来自大肠杆菌的二氢蝶呤合酶的抑制剂。许多6-（烷基氨基）-5-亚硝基异胞嘧啶在体外具有与合成酶的治疗有效磺酰胺抑制剂相当或更高的体外效力。已知磺酰胺类药物会竞争合酶的对氨基苯甲酸结合位点，并通过6-（甲基氨基）-5-亚硝基异胞嘧啶（16; I50 = 1.6 microM）和6- （3-苯氧丙基）氨基类似物（33; I50 = 3.7 microM）表明亚硝基异胞嘧啶抑制剂与蝶啶底物竞争该酶。结构活性研究表明，酶表面对异胞嘧啶6-氨基功能周围区域的空间体积具有较低的耐受性。然而，这种空间不耐受性可以通过具有6-（ω-苯基烷基）氨基取代基的某些类似物实现的正构构相互作用而在很大程度上抵消。例如，6-[（（7-苯基庚基）氨基] -5-亚硝基异胞嘧啶（28）与6-甲基氨基化合物16一样有效（I50 = 1.4 microM）抑制剂。尽管5-亚硝基

  DOI：

  10.1021/jm00150a019
• 作为产物：
  描述：

  6-chloro-4-N-ethylpyrimidine-2,4-diamine 在 盐酸 、 甲醇 、 乙醇 作用下， 生成 2-氨基-6-(乙基氨基)-4(1H)-嘧啶酮
  参考文献：
  名称：

  Effects of Transdermal Testosterone on Cognitive Function and Health Perception in Older Men With Low Bioavailable Testosterone Levels

  摘要：

  Background. Many men older than 50 years have bioavailable testosterone levels below the reference range for young adult men. The impact of the decreased androgen levels oil cognition and health perception has received little attention.Methods. Sixty-seven men (mean age 76 +/- 4 years, range 65-87) with bioavailable testosterone levels below 128 ng/dl (lower limit for adult normal range) were randomized to receive transdermal testosterone (2-2.5 mg patches/d) or placebo patches for I year. All men received 500 mg Supplemental calcium and 400 IU vitamin D. Outcome measures included sex hormones [testosterone, bioavailable testosterone, sex hormone binding globulin (SHBG), estradiol, and estrone], cognitive tests, (Digit Symbol, Digit Span, Trailmaking A and B), health perception (Medical Outcome Survey Short-form 36 or SF-36), lower extremity muscle strength and power. and calcium intake.Results. Twenty-three men (34%) withdrew from the Study; 44 men completed the trial. Bioavailable testosterone levels increased from 93 +/- 34 (SD) to 162 +/- 100 ng/dl (p < .002) at 12 months in the testosterone group (n = 24) while no change occurred in the control group (n 20). While there was no change in estradiol levels in either group, estrone levels increased in the testosterone group (28 +/- 7 to 32 +/- 9 pg/dl, p = .017). Scores oil the Digit Symbol test improved in both the testosterone and placebo groups. Scores on Trailmaking B improved in men treated with testosterone (p < .005), although the changes were not statistically different from the changes seen in the placebo group. Twelve-month scores on Trailmaking B for the entire group were correlated with 12-month testosterone levels (p = .016). Scores for health perception measured by SF-36 did not change significantly, though scores of mental and general health declined in both groups during the 12-month intervention. Twelve-month bioavailable testosterone scores were directly correlated with scores for physical role (p = .022), vitality (p = .036), and the physical composite score (p = .010).Conclusions. Transdermal testosterone treatment in men with low bioavailable testosterone levels does not impair and may improve cognitive function. Treatment did not improve health perception but this may have been due to the side effects of skin irritation suggested by similar reactions in both the testosterone and placebo groups.

  DOI：

  10.1093/gerona/57.5.m321

文献信息

• Alkylpurines as immunopotentiating agents. Synthesis and antiviral activity of certain alkylguanines
  作者：Maged A. Michael、Howard B. Cottam、Donald F. Smee、Roland K. Robins、Ganesh D. Kini

  DOI：10.1021/jm00074a025

  日期：1993.10

  Several simple 8-substituted 9-alkyl- and 7,8-disubstituted 9-alkylguanine derivatives were synthesized as potential antiviral agents. These were tested for antiviral protection against a lethal Semliki Forest virus (SFV) infection in mice, and their antiviral properties were evaluated from a structure-activity standpoint. In this model system, 9-alkylguanines with the alkyl chain consisting of four

  合成了几种简单的8-取代的9-烷基-和7,8-二取代的9-烷基鸟嘌呤衍生物作为潜在的抗病毒药。测试了它们在小鼠中对致命的Semliki森林病毒（SFV）感染的抗病毒保护作用，并从结构活性的角度评估了它们的抗病毒特性。在该模型系统中，发现烷基链由4至6个碳组成的9-烷基鸟嘌呤活性最高。除7-烷基-8-氧代取代基外，嘌呤环8-位的取代没有增强活性。发现这些数据支持以下假设：鸟嘌呤不需要包含完整的碳水化合物部分，从而凭借免疫增强作用而表现出抗病毒活性。因此，
• An improved procedure for the preparation of 2-amino-8-alkylpyrido-[2,3-<i>d</i>]pyrimidin-4(3<i>H</i>)-ones (8-alkyl-N5-deazapterins)
  作者：Michael T. G. Ivery、Jill E. Gready

  DOI：10.1002/jhet.5570310615

  日期：1994.11

  We report an improved procedure for the preparation of 8-alkyl-N5-deazapterins which allows clean preparation of all ring-methyl substituted compounds, including 5- and 7-methyl substituted compounds. The procedure was also successfully applied to the preparation of N5-deazapterins with improved yield over previous reports. The uv/visible and pKa data confirm the predicted increased basicity of 8-

  我们报告了一个改进的程序，用于制备8-烷基-N5-脱氮杂环丁烷，它允许干净地制备所有环甲基取代的化合物，包括5-和7-甲基取代的化合物。该方法还成功地用于制备N5-脱氮杂陈蛋白，其收率比以前的报告有所提高。uv / visible和p K a数据证实了与N5-deazapterin亲本相比，预计的8-烷基-N5-deazapterins碱性增加，并且表明N5-deazapterins在N8上质子化，而8-烷基-N5-deazapterins在N3上质子化。 。
• [EN] 8-SUBSTITUTED-N5-DEAZAPTERINS AS ANTIFOLATES<br/>[FR] N5-DESAZAPTERINES SUBSTITUEES EN POSITION 8, UTILISEES COMME ANTIFOLATES
  申请人：THE UNIVERSITY OF SYDNEY

  公开号：WO1993020075A1

  公开（公告）日：1993-10-14

  (EN) A method of designing compounds which bind to the enzyme dihydrofolate reductase (DHFR), N5-deazapterin compounds of formula (I) which are useful for inhibiting DHFR and methods of selecting and preparing such compounds using theoretical calculations. Compounds of formula (I), pharmaceutically acceptable salts or esters thereof, wherein R1 is hydrogen or alkyl optionally substituted by hydroxy, thio or halogen; R2 is H, -CHO, -COOH, alkyl, CH(Oalk)2, alkyl substituted by hydroxy, thio, halogen, PABA, PABA-Glu; alkenyl, alkynyl; R3 is H, alkyl; R4 is alkyl optionally substituted by hydroxy, thio, halogen; alkenyl, alkynyl; X- is halogen.(FR) Procédé permettant de développer des composés qui se lient à l'enzyme de dihydrofolate réductase (DHFR), composés de N5-désazaptérine de la formule (I) utilisés pour inhiber la DHFR et procédés de sélection et de préparation de tels composés à l'aide de calculs théoriques. Composés de la formule (I), leurs sels ou esters pharmaceutiquement acceptables, formule dans laquelle R1 représente hydrogène ou alkyle éventuellement substitué par hydroxy, thio ou halogène; R2 représente H, -CHO, -COOH, alkyle, CH(Oalk)2, alkyle substitué par hydroxy, thio, halogène, PABA, PABA-Glu, alcényle, alcynyle; R3 représente H, alkyle; R4 représente alkyle éventuellement substitué par hydroxy, thio, halogène, alcényle, alcynyle; X- représente halogène.
• Monocyclic pteridine analogs. Inhibition of Escherichia coli dihydropteroate synthase by 6-amino-5-nitrosoisocytosines
  作者：O. William Lever、Lawrence N. Bell、H. Michael McGuire、Robert Ferone

  DOI：10.1021/jm00150a019

  日期：1985.12

  inhibitors of dihydropteroate synthase from Escherichia coli. A number of 6-(alkylamino)-5-nitrosoisocytosines have in vitro potency equivalent with or superior to that of therapeutically effective sulfonamide inhibitors of the synthase. The sulfonamide drugs are known to compete for the p-aminobenzoic acid binding site of the synthase, and kinetic analysis of inhibition of the synthase by 6-(methyl

  在体外评价了多种5，6-二取代的异胞嘧啶衍生物作为来自大肠杆菌的二氢蝶呤合酶的抑制剂。许多6-（烷基氨基）-5-亚硝基异胞嘧啶在体外具有与合成酶的治疗有效磺酰胺抑制剂相当或更高的体外效力。已知磺酰胺类药物会竞争合酶的对氨基苯甲酸结合位点，并通过6-（甲基氨基）-5-亚硝基异胞嘧啶（16; I50 = 1.6 microM）和6- （3-苯氧丙基）氨基类似物（33; I50 = 3.7 microM）表明亚硝基异胞嘧啶抑制剂与蝶啶底物竞争该酶。结构活性研究表明，酶表面对异胞嘧啶6-氨基功能周围区域的空间体积具有较低的耐受性。然而，这种空间不耐受性可以通过具有6-（ω-苯基烷基）氨基取代基的某些类似物实现的正构构相互作用而在很大程度上抵消。例如，6-[（（7-苯基庚基）氨基] -5-亚硝基异胞嘧啶（28）与6-甲基氨基化合物16一样有效（I50 = 1.4 microM）抑制剂。尽管5-亚硝基
• Effects of Transdermal Testosterone on Cognitive Function and Health Perception in Older Men With Low Bioavailable Testosterone Levels
  作者：A. M. Kenny、S. Bellantonio、C. A. Gruman、R. D. Acosta、K. M. Prestwood

  DOI：10.1093/gerona/57.5.m321

  日期：2002.5.1

  Background. Many men older than 50 years have bioavailable testosterone levels below the reference range for young adult men. The impact of the decreased androgen levels oil cognition and health perception has received little attention.Methods. Sixty-seven men (mean age 76 +/- 4 years, range 65-87) with bioavailable testosterone levels below 128 ng/dl (lower limit for adult normal range) were randomized to receive transdermal testosterone (2-2.5 mg patches/d) or placebo patches for I year. All men received 500 mg Supplemental calcium and 400 IU vitamin D. Outcome measures included sex hormones [testosterone, bioavailable testosterone, sex hormone binding globulin (SHBG), estradiol, and estrone], cognitive tests, (Digit Symbol, Digit Span, Trailmaking A and B), health perception (Medical Outcome Survey Short-form 36 or SF-36), lower extremity muscle strength and power. and calcium intake.Results. Twenty-three men (34%) withdrew from the Study; 44 men completed the trial. Bioavailable testosterone levels increased from 93 +/- 34 (SD) to 162 +/- 100 ng/dl (p < .002) at 12 months in the testosterone group (n = 24) while no change occurred in the control group (n 20). While there was no change in estradiol levels in either group, estrone levels increased in the testosterone group (28 +/- 7 to 32 +/- 9 pg/dl, p = .017). Scores oil the Digit Symbol test improved in both the testosterone and placebo groups. Scores on Trailmaking B improved in men treated with testosterone (p < .005), although the changes were not statistically different from the changes seen in the placebo group. Twelve-month scores on Trailmaking B for the entire group were correlated with 12-month testosterone levels (p = .016). Scores for health perception measured by SF-36 did not change significantly, though scores of mental and general health declined in both groups during the 12-month intervention. Twelve-month bioavailable testosterone scores were directly correlated with scores for physical role (p = .022), vitality (p = .036), and the physical composite score (p = .010).Conclusions. Transdermal testosterone treatment in men with low bioavailable testosterone levels does not impair and may improve cognitive function. Treatment did not improve health perception but this may have been due to the side effects of skin irritation suggested by similar reactions in both the testosterone and placebo groups.