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5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one | 871671-45-3

中文名称
——
中文别名
——
英文名称
5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
英文别名
5-phenyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one;5-Phenyl-1,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one化学式
CAS
871671-45-3
化学式
C12H9N3O
mdl
——
分子量
211.223
InChiKey
DPFDUWXYLLEHIJ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.5
  • 重原子数:
    16
  • 可旋转键数:
    1
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    57.2
  • 氢给体数:
    2
  • 氢受体数:
    2

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    腺苷激酶抑制剂。6.在C4处被甘氨酰胺和相关化合物取代的5-苯基-7-(5-脱氧-β-D-核呋喃糖基)吡咯并[2,3-d]嘧啶的合成,水溶性和抗伤害作用。
    摘要:
    4-(苯氨基)-5-苯基-7-(5-脱氧-β-D-呋喃呋喃糖基)吡咯并[2,3-d]嘧啶1和相关化合物被称为“二芳基丁二醛”类似物,是腺苷激酶(AK)的有效抑制剂。 ),并且在疼痛动物模型(例如大鼠福尔马林爪模型(GP3269 ED50 = 6.4 mg / kg))中具有口服活性。但是,该化合物类别的实用性受到水溶性差的限制,这可归因于固态的平行C4和C5芳基环的堆叠(化合物1和GP3269的pH 7.4溶解度< 0.05微克/毫升)。为了增加水溶性,疏水性C 4-苯基氨基取代基被更亲水的甘氨酰胺取代。该修饰导致改善的水溶性,同时保持AK抑制效力。研究了类似物,其中甘氨酰胺部分的变化与碱基和糖的变化结合在一起。铅化合物4-N-(N-环丙基氨基甲酰基甲基)氨基-5-苯基-7-(5-脱氧-β-D-呋喃呋喃糖基)吡咯并[2,3-d]嘧啶(16c)(IC50 = 3 nM在pH 7.4时,水溶解度=
    DOI:
    10.1021/jm050394a
  • 作为产物:
    描述:
    4-氯-5-碘-7H-吡咯并[2,3-d]嘧啶ammonium hydroxide三甲基氯硅烷 、 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 sodium hydride 、 sodium carbonate 、 三氟乙酸 、 sodium iodide 作用下, 以 甲醇二氯甲烷N,N-二甲基甲酰胺乙腈 为溶剂, 反应 22.0h, 生成 5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
    参考文献:
    名称:
    2,6-取代的7-(Het)芳基-7-脱氮嘌呤核碱基(2,4-二取代的5-(Het)芳基-吡咯并[2,3-d]嘧啶的合成)
    摘要:
    作为“杂环合成的现代策略”专题的一部分发布 抽象的 一系列的7-(杂)芳基- 7-脱氮嘌呤核碱基(5 - [(杂)芳基] -2,4-二取代的7 ħ吡咯并[2,3- d ]嘧啶)轴承NH 2,青梅,SME,Suzuki-Miyaura水溶液通过SEM保护的7-碘-7-脱氮嘌呤与(杂)芳基硼酸的水相Suzuki-Miyaura交叉偶联反应,然后脱保护,可制备6位的Me或Me基以及2位的H,NH 2或Me。通过O-去甲基化反应,将6-甲氧基衍生物进一步转化为7-脱氮杂黄嘌呤或7-脱氮鸟嘌呤。不同于它们的核糖核苷对应物,7-脱氮嘌呤核苷碱基没有发挥任何明显的细胞抑制或抗病毒作用。 一系列的7-(杂)芳基- 7-脱氮嘌呤核碱基(5 - [(杂)芳基] -2,4-二取代的7 ħ吡咯并[2,3- d ]嘧啶)轴承NH 2,青梅,SME,Suzuki-Miyaura水溶液通过SEM保护的7-碘-7-脱氮嘌
    DOI:
    10.1055/s-0036-1588443
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文献信息

  • [EN] MAP4K4 INHIBITORS<br/>[FR] INHIBITEURS DE MAP4K4
    申请人:IMPERIAL INNOVATIONS LTD
    公开号:WO2019073253A1
    公开(公告)日:2019-04-18
    This invention relates to pyrrolopyrimidine comprising compounds that may be useful as inhibitors of Mitogen-activated Protein Kinase Kinase Kinase Kinase-4 (MAP4K4). The invention also relates to the use of these pyrrolopyrimidine comprising compounds, for example in a method of treatment. There are also provided processes for producing compounds of the present invention and method of their use. In particular, the present invention relates to compounds of formula (I).
    这项发明涉及含有吡咯吡嘧啶的化合物,这些化合物可能作为丝裂原活化蛋白激酶激酶激酶激酶-4(MAP4K4)的抑制剂而有用。该发明还涉及利用这些含有吡咯吡嘧啶的化合物,例如在治疗方法中的使用。还提供了生产本发明化合物的方法以及它们的使用方法。具体而言,本发明涉及式(I)的化合物。
  • Facile Methods for the Synthesis of 5-Aryl and 5-Iodo Pyrrolo[2,3-<i>d</i>]pyrimidines
    作者:K. Venkata Rao、M. Raghu Prasad、A. Raghuram Rao
    DOI:10.1002/jhet.1937
    日期:2014.8
    environmentally benign one-pot method has been developed for the synthesis of 4-amino-5-arylpyrrolo[2,3-d]pyrimidines. Phthalimido acetophenones were reacted with cyanoacetamide to give 2-amino-4-phenyl-1H-pyrrole-3-carboxamides, which were further converted to 5-aryl-3H-pyrrolo[2,3-d]pyrimidin-4-ones. A novel method is also developed for the synthesis of 4-amino-5-iodopyrrolo[2,3-d]pyrimidines.
    已经开发出一种有效且环境友好的一锅法,用于合成4-氨基-5-芳基吡咯并[2,3- d ]嘧啶。邻苯二甲酰亚胺苯乙酮与氰基乙酰胺,得到2-氨基-4-苯基-1- ħ吡咯-3-甲酰胺,其进一步转化为5-芳基-3- ħ吡咯并[2,3- d ]嘧啶-4-酮。还开发了用于合成4-氨基-5-碘吡咯并[2,3- d ]嘧啶的新方法。
  • Selective Inhibitors of Bacterial t-RNA-(N<sup>1</sup>G37) Methyltransferase (TrmD) That Demonstrate Novel Ordering of the Lid Domain
    作者:Pamela J. Hill、Ayome Abibi、Robert Albert、Beth Andrews、Moriah M. Gagnon、Ning Gao、Tyler Grebe、Laurel I. Hajec、Jian Huang、Stephania Livchak、Sushmita D. Lahiri、David C. McKinney、Jason Thresher、Hongming Wang、Nelson Olivier、Ed T. Buurman
    DOI:10.1021/jm400718n
    日期:2013.9.26
    The tRNA-(N(1)G37) methyltransferase (TrmD) is essential for growth and highly conserved in both Gram-positive and Gram-negative bacterial pathogens. Additionally, TrmD is very distinct from its human orthologue TRM5 and thus is a suitable target for the design of novel antibacterials. Screening of a collection of compound fragments using Haemophilus influenzae TrmD identified inhibitory, fused thieno-pyrimidones that were competitive with S-adenosylmethionine (SAM), the physiological methyl donor substrate. Guided by X-ray cocrystal structures, fragment 1 was elaborated into a nanomolar inhibitor of a broad range of Gram-negative TrmD isozymes. These compounds demonstrated no activity against representative human SAM utilizing enzymes, PRMT1 and SET7/9. This is the first report of selective, nanomolar inhibitors of TrmD with demonstrated ability to order the TrmD lid in the absence of tRNA.
  • MAP4K4 INHIBITORS
    申请人:IMPERIAL COLLEGE OF SCIENCE, TECHNOLOGY AND MEDICINE
    公开号:US20200339583A1
    公开(公告)日:2020-10-29
    This invention relates to pyrrolopyrimidine comprising compounds that may be useful as inhibitors of Mitogen-activated Protein Kinase Kinase Kinase Kinase-4 (MAP4K4). The invention also relates to the use of these pyrrolopyrimidine comprising compounds, for example in a method of treatment. There are also provided processes for producing compounds of the present invention and method of their use. In particular, the present invention relates to compounds of formula (I).
  • Adenosine Kinase Inhibitors. 6. Synthesis, Water Solubility, and Antinociceptive Activity of 5-Phenyl-7-(5-deoxy-β-<scp>d</scp>-ribofuranosyl)pyrrolo[2,3-<i>d</i>]pyrimidines Substituted at C4 with Glycinamides and Related Compounds
    作者:Brett C. Bookser、Bheemarao G. Ugarkar、Michael C. Matelich、Robert H. Lemus、Matthew Allan、Megumi Tsuchiya、Masami Nakane、Atsushi Nagahisa、James B. Wiesner、Mark D. Erion
    DOI:10.1021/jm050394a
    日期:2005.12.1
    4-(Phenylamino)-5-phenyl-7-(5-deoxy-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 1 and related compounds known as "diaryltubercidin" analogues are potent inhibitors of adenosine kinase (AK) and are orally active in animal models of pain such as the rat formalin paw model (GP3269 ED50= 6.4 mg/kg). However, the utility of this compound class is limited by poor water solubility that can be attributed
    4-(苯氨基)-5-苯基-7-(5-脱氧-β-D-呋喃呋喃糖基)吡咯并[2,3-d]嘧啶1和相关化合物被称为“二芳基丁二醛”类似物,是腺苷激酶(AK)的有效抑制剂。 ),并且在疼痛动物模型(例如大鼠福尔马林爪模型(GP3269 ED50 = 6.4 mg / kg))中具有口服活性。但是,该化合物类别的实用性受到水溶性差的限制,这可归因于固态的平行C4和C5芳基环的堆叠(化合物1和GP3269的pH 7.4溶解度< 0.05微克/毫升)。为了增加水溶性,疏水性C 4-苯基氨基取代基被更亲水的甘氨酰胺取代。该修饰导致改善的水溶性,同时保持AK抑制效力。研究了类似物,其中甘氨酰胺部分的变化与碱基和糖的变化结合在一起。铅化合物4-N-(N-环丙基氨基甲酰基甲基)氨基-5-苯基-7-(5-脱氧-β-D-呋喃呋喃糖基)吡咯并[2,3-d]嘧啶(16c)(IC50 = 3 nM在pH 7.4时,水溶解度=
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