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N-苄基-2-氯-9H-嘌呤-6-胺 | 39639-47-9

中文名称
N-苄基-2-氯-9H-嘌呤-6-胺
中文别名
6-苄基氨基-2-氯嘌呤
英文名称
N-benzyl-2-chloro-9H-purin-6-amine
英文别名
6-benzylamino-2-chloropurine;N-benzyl-2-chloro-7H-purin-6-amine
N-苄基-2-氯-9H-嘌呤-6-胺化学式
CAS
39639-47-9
化学式
C12H10ClN5
mdl
——
分子量
259.698
InChiKey
IJKBYBPPNNHJSF-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

物化性质

  • 熔点:
    239-241℃
  • 沸点:
    407.7±55.0 °C(Predicted)
  • 密度:
    1.49
  • 溶解度:
    可溶于氯仿、DMSO、乙酸乙酯

计算性质

  • 辛醇/水分配系数(LogP):
    2.9
  • 重原子数:
    18
  • 可旋转键数:
    3
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.08
  • 拓扑面积:
    66.5
  • 氢给体数:
    2
  • 氢受体数:
    4

安全信息

  • 海关编码:
    2933990090
  • 危险性防范说明:
    P280,P305+P351+P338
  • 危险性描述:
    H302
  • 储存条件:
    2-8°C

SDS

SDS:930c78eb21cdb401048f8e4d8f3dd96f
查看

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
    N-苄基-2-氯-9-甲基-9H-嘌呤-6-胺 N-benzyl-2-chloro-9-methyl-9H-purin-6-amine 101622-53-1 C13H12ClN5 273.725
    N-苄基-2-氯-9-异丙基-9h-嘌呤-6-胺 N-benzyl-2-chloro-9-isopropyl-9H-purin-6-amine 186692-41-1 C15H16ClN5 301.779
    —— 2-chloro-6-benzylamino-9-(2-propynyl)purine 1314172-32-1 C15H12ClN5 297.747
    N-苄基-9-丁基-2-氯-9H-嘌呤-6-胺 N-benzyl-9-butyl-2-chloro-9H-purin-6-amine 1007556-16-2 C16H18ClN5 315.805
    —— 3-[6-(Benzylamino)-2-chloropurin-9-yl]propan-1-ol 1007556-20-8 C15H16ClN5O 317.778
    —— N,9-dibenzyl-2-chloropurin-6-amine 1007556-15-1 C19H16ClN5 349.823
    —— N2,N6-dibenzyl-7(9)H-purine-2,6-diamine 39639-54-8 C19H18N6 330.392
    —— 2-(2-hydroxyethylamino)-6-benzylaminopurine 70608-06-9 C14H16N6O 284.321
    2-叠氮-6-苄基氨基嘌呤 2-azido-6-benzylaminopurine 61716-00-5 C12H10N8 266.265
    —— N-benzyl-2-chloro-9-cyclopentyl-9H-purin-6-amine 310400-99-8 C17H18ClN5 327.816
    • 1
    • 2
    • 3

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Cytokinin-Derived Cyclin-Dependent Kinase Inhibitors:  Synthesis and cdc2 Inhibitory Activity of Olomoucine and Related Compounds
    摘要:
    Cyclin-dependent kinases (cdk) have recently raised considerable interest in view of their essential role in the regulation of the cell division cycle. The structure-activity relationships of cdk inhibition showed that the 1, 3, and 7 positions of the purine ring must remain free, probably for a direct interaction, in which it behaves as a hydrogen bond acceptor. Olomoucine (6-(benzylamino)-2-[(2-hydroxyethyl)amino]-9-methylpurine, OC), roscovitine (6-(benzylamino)-2(R)-[[1-(hydroxymethyl)propyl]amino]-9-isopropylpurine), and other N-6,2,9-trisubstituted adenines were found to exert a strong inhibitory effect on the p34(cdc2)/cyclin B kinase. Removal or change of the side chain at position 2 or the hydrophobic group at position 9 dramatically decreased the inhibitory activity of olomoucine or roscovitine. Inhibition of cdk with OC and related compounds clearly arrests cell proliferation of many tumor cell lines at G(1)/S and G(2)/M transitions and also triggers apoptosis in the target tumor cells in vitro and in vivo. Thus, from a pharmacological point of view, OC may represent a model compound for a new class of antimitotic and antitumor drugs.
    DOI:
    10.1021/jm960666x
  • 作为产物:
    描述:
    鸟嘌呤盐酸 、 sodium hydroxide 、 zinc(II) chloride 、 sodium nitrite 、 三氯氧磷 作用下, 以 1,2-二氯乙烷异丙醇 为溶剂, 反应 20.0h, 生成 N-苄基-2-氯-9H-嘌呤-6-胺
    参考文献:
    名称:
    轻松合成8-叠氮基-6-苄基氨基嘌呤。
    摘要:
    在AcONa存在下,在AcOH中用Br 2将6-苄氨基嘌呤(1)溴化,以59%的收率得到6-苄氨基-8-溴嘌呤(2)。通过与NaN 3在二甲亚砜中反应,将溴化物2直接转化为8-叠氮基-6-苄氨基嘌呤(3),将溴化物2直接转化,并将其性能与已知化合物2-叠氮基-2-比较,从而确定了溴化位置。6-苄基氨基嘌呤(11)。化合物3和11根据活体植物的主要细胞分裂素效应,在特定的生物测试中检查了它们的生物活性。两种合成的化合物均显示出与典型的细胞分裂素6-苄基氨基嘌呤(1)相似的效果。
    DOI:
    10.1080/15257770.2011.602655
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文献信息

  • Novel purine derivatives, preparation method and use as medicines
    申请人:Aventis Pharma S.A.
    公开号:US20040063732A1
    公开(公告)日:2004-04-01
    The use of purine derivatives of formula (I): 1 as cdk kinase inhibitors for the prevention and treatment of fungal infections. Also disclosed are novel methods and intermediates for the production of compounds of formula I, as well as pharmaceutical compositions containing said compounds.
    将式(I)的嘌呤衍生物用作CDK激酶抑制剂,用于预防和治疗真菌感染。还公开了用于制备式(I)化合物的新方法和中间体,以及含有该化合物的药物组合物。
  • Substituted xanthines and cytokinin analogues as inhibitors of cytokinin N-glucosylation
    作者:Charles H. Hocart、David S. Letham、Charles W. Parker
    DOI:10.1016/0031-9422(91)85086-f
    日期:1991.1
    raising the amount of free BAP. N -glucosylation of BAP in radish leaves was found to be suppressed most effectively by 1,7-dimethyl-3-(3-methylbutyl)xanthine, 1,7-dimethyl-3-(5-hexenyl)xanthine and 1,7-dimethyl-3-(3-methyl-2-butenyl)xanthine. The first two compounds were also effective inhibitors in radish cotyledons and elevated the concentrations of both free BAP and BAP nucleotide. These results
    摘要 合成了一系列 3-取代黄嘌呤、2-(2-羟基-2-甲基丙基氨基)-9-甲基-6-苄氨基嘌呤和 7-苄氨基恶唑并[5,4-d]嘧啶作为细胞分裂素 N-葡萄糖基化的潜在抑制剂。 . 在玉米叶片段中,发现后一种化合物是测试的最有效抑制剂,可抑制 6-苄氨基嘌呤 (BAP) 的 9-葡糖苷的形成并增加游离 BAP 的量。发现萝卜叶中 BAP 的 N-葡萄糖基化被 1,7-二甲基-3-(3-甲基丁基)黄嘌呤、1,7-二甲基-3-(5-己烯基)黄嘌呤和 1,7-二甲基-3-(3-甲基-2-丁烯基)黄嘌呤。前两种化合物也是萝卜子叶的有效抑制剂,并提高了游离 BAP 和 BAP 核苷酸的浓度。
  • [EN] COMPOUNDS AS INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR<br/>[FR] COMPOSÉS EN TANT QU'INHIBITEURS DU FACTEUR INHIBITEUR DE LA MIGRATION DES MACROPHAGES
    申请人:IMMUNOPHAGE BIOMEDICAL CO LTD
    公开号:WO2020186220A1
    公开(公告)日:2020-09-17
    The present invention provides compounds of Formula (I) shown above and their pharmaceutically acceptable salt, solvates, isomers, or prodrugs, as well as pharmaceutical compositions containing these compounds. Also provided by the invention is a method for treating a disorder mediated by macrophage migration inhibitory factor in a subject, comprising administering to the subject in need thereof a compound or a pharmaceutical composition of this invention.
    本发明提供了上述公式(I)所示的化合物及其药用可接受的盐、溶剂化物、异构体或前药,以及含有这些化合物的药物组合物。本发明还提供了一种用于治疗由巨噬细胞迁移抑制因子介导的疾病的方法,包括向需要治疗的对象施用本发明的化合物或药物组合物。
  • Method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK)
    申请人:CHEN Han-Min
    公开号:US20140303112A1
    公开(公告)日:2014-10-09
    The present invention relates to a method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK) and the use of the compounds in the prevention or treatment of disease, including pre-diabetes, type 2 diabetes, syndrome X, metabolic syndrome and obesity.
    本发明涉及一种治疗疾病或病情的方法,该疾病或病情容易通过AMPK激活剂和公式化合物得到改善,这些化合物有助于激活AMP激活蛋白激酶(AMPK),并将这些化合物用于预防或治疗疾病,包括糖尿病前期、2型糖尿病、X综合症、代谢综合征和肥胖症。
  • 2,6,9-三取代嘌呤衍生物及其制备方法与应 用
    申请人:中国人民解放军军事医学科学院放射与辐射 医学研究所
    公开号:CN104936959B
    公开(公告)日:2018-09-18
    提供式I所示的2,6,9‑三取代嘌呤衍生物及其制备方法与应用,其中R1、R2、R3和R4如说明书中所定义。体外细胞试验证明所述化合物能有效抑制多种肿瘤细胞的生长,可发展为抗肿瘤药物;动物实验证明所述化合物在体内具有显著的抗EV71病毒作用,可发展为治疗和预防EV71病毒感染的药物。
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