2-chloro-N,N-diethylpyrimidin-4-amine | 62968-41-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-chloro-N,N-diethylpyrimidin-4-amine
• 英文别名: 2-Chloro-4-(diethylamino)pyrimidine
• CAS: 62968-41-6
• 化学式: C₈H₁₂ClN₃
• 分子量: 185.656
• InChiKey: IJBXLOODPFVVJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险类别：
  8
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P310,P330,P332+P313,P362,P403+P233,P405,P501
• 危险品运输编号：
  2735
• 危险性描述：
  H302,H315,H318,H335
• 包装等级：
  III
• 储存条件：
  | 室温 |

反应信息

• 作为反应物：
  描述：

  2-chloro-N,N-diethylpyrimidin-4-amine 在 盐酸 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 14.0h， 生成 N⁴,N⁴-diethyl-N²-(4-(3-(piperidin-1-yl)propoxy)phenyl)pyrimidine-2,4-diamine
  参考文献：
  名称：

  Discovery and SAR studies of novel 2-anilinopyrimidine-based selective inhibitors against triple-negative breast cancer cell line MDA-MB-468

  摘要：

  Triple-negative breast cancers (TNBCs) are characterized as an invasive and intractable subtype of breast cancers. Overexpression of epidermal growth factor receptor (EGFR) has been considered to be an important target for TNBC therapy, but efficacies of EGFR inhibitors in clinical trials are elusive. In this study, novel series of 2-anilinopyrimidines were synthesized in an effort to identify selective inhibitors against an EGFR-overexpressing TNBC cell line. Biological evaluation demonstrated that compounds 21 and 38, with a 4-methylpiperidine group and a high ClogP value, exhibited good potency and selectivity for the TNBC cell line. This study has provided evidence to support further development of 2-anilinopyrimidine-based TNBC selective inhibitors and investigation of the targets of compounds 21 and 38.

  DOI：

  10.1016/j.bmcl.2018.11.010
• 作为产物：
  描述：

  5-Bromo-2-chloro-N,N-diethylpyrimidin-4-amine 以42%的产率得到
  参考文献：
  名称：

  STREKOWSKI L.; DWORNICZAK M.; KOWALEWSKI A., POL. J. CHEM., 1980, 54, NO 7-8, 1557-1562

  摘要：

  DOI：

文献信息

• Photoredox Catalyzed Dealkylative Aromatic Halogen Substitution with Tertiary Amines
  作者：Dmitry L. Lipilin、Alexander E. Frumkin、Alexey Y. Tyurin、Vitalij V. Levin、Alexander D. Dilman

  DOI：10.3390/molecules26113323

  日期：——

  A reaction of aromatic halides bearing electron-withdrawing groups with tertiary amines in the presence of an iridium catalyst under blue light irradiation is described. Products of the aromatic substitution of the halide by the dialkylamino fragment are obtained. The interaction of aryl radicals with tertiary amines to generate zwitterionic radical species is believed to be the key factor responsible

  描述了带有吸电子基团的芳香族卤化物与叔胺在铱催化剂存在下在蓝光照射下的反应。获得卤化物被二烷基氨基片段芳族取代的产物。芳基自由基与叔胺相互作用产生两性离子自由基物种被认为是影响反应效率的关键因素。
• Pyrimidinyl Biphenylureas: Identification of New Lead Compounds as Allosteric Modulators of the Cannabinoid Receptor CB₁
  作者：Leepakshi Khurana、Bo-Qiao Fu、Anantha L. Duddupudi、Yu-Hsien Liao、Sri Sujana Immadi、Debra A. Kendall、Dai Lu

  DOI：10.1021/acs.jmedchem.6b01448

  日期：2017.2.9

  cannabinoid receptor 1 (CB1) and antagonized G protein coupling. This compound demonstrated potent anorectic effects similar to the CB1 antagonist rimonabant that once was marketed for the treatment of obesity, suggesting a new chemical entity for the discovery of antiobesity drugs. To increase structural diversity of this class of CB1 ligands, we designed and synthesized two classes of novel analogues

  变构调节剂1-（4-氯苯基）-3-（3-（6-（吡咯烷基-1-基）吡啶-2-基）苯基）脲（PSNCBAM- 1，2）结合了大麻素受体1（CB 1）和拮抗的G蛋白偶联。该化合物表现出有效的厌食作用，类似于曾经出售用于治疗肥胖症的CB 1拮抗剂利莫那班，这为发现抗肥胖药提供了新的化学实体。为了增加这类CB 1配体的结构多样性，我们设计并合成了两类新型类似物，其中2的吡啶环被嘧啶环取代。这些积极地调节了CB 1的结合正构激动剂CP55,940，同时表现出对G蛋白偶联活性的拮抗作用。有趣的是，化合物7d和8d表现出通过β-arrestin介导的ERK1 / 2磷酸化，而正构CP55940则以G蛋白依赖性方式发生。这些可以用作未来CB 1变构调节剂发展的新的先导化合物，它们通过新的机理表现出偏向激动性和潜在的抗肥胖行为。
• SAR optimization studies on a novel series of 2-anilinopyrimidines as selective inhibitors against triple-negative breast cancer cell line MDA-MB-468
  作者：Jeyun Jo、Heegyu Kim、Ji Youn Oh、Soyeong Kim、Yeong Hye Park、Hyeonjin Choi、Jee-Yeong Jeong、Young-Suk Jung、Hwayoung Yun

  DOI：10.1016/j.bmcl.2019.126752

  日期：2019.12

  synthesized two series of 2-anilinopyrimidines based on the structure of our previously reported compound 1 that act as a selective inhibitor of the basal-like TNBC cell line MDA-MB-468. Through the fine-tuning of 1, cyclic and acyclic amines at 4-position of the pyrimidine core were turned out to be crucial for the selectivity. An extensive analysis of structure-activity relationships of the analogs revealed

  三阴性乳腺癌（TNBC）约占乳腺癌病例的15％，并且表现出侵略性的临床行为。在这项研究中，我们基于先前报道的化合物1的结构设计和合成了两个系列的2-苯胺基嘧啶，它们可作为基础样TNBC细胞系MDA-MB-468的选择性抑制剂。通过对1的精细调节，发现嘧啶核4位的环状和无环胺对于选择性至关重要。对类似物的结构-活性关系的广泛分析表明，丙基链末端的氨基烷基易于修饰。在新合成的类似物中，带有4-氯哌啶和环己基的化合物38被发现是最有效和最具选择性的，
• Substituted amidoalkyl uracils and their use as inhibitors of the poly(adp-ribose) synthetase (pars)
  申请人：Albrecht Barbara

  公开号：US20050075347A1

  公开（公告）日：2005-04-07

  The invention relates to novel amidoalkyl uracil derivatives of formula (I), to a method for the production thereof, and to their use as medicament active substances for the prophylaxis and/or treatment of medical disorders.

  该发明涉及到化合物的新型酰胺烷基尿嘧啶衍生物（I）的公式，以及它们的生产方法，以及它们作为药物活性物质用于预防和/或治疗医学疾病。
• Substituted amidoalkyl uracils and their use as inhibitors of the poly(adp-ribose) synthetase (PARS)
  申请人：Bayer Aktiengesellschaft

  公开号：US07125995B2

  公开（公告）日：2006-10-24

  This application relates to compounds of formula (I) below in which the several variable groups are as defined in the specification and claims, to methods of preparing these materials, to pharmaceutical compositions containing these materials, and to methods of using these materials to treat ischaemia or reperfusion damage.

  本申请涉及以下式子（I）的化合物，其中各个可变基团在说明书和权利要求中定义，涉及制备这些材料的方法，含有这些材料的制药组合物，以及使用这些材料治疗缺血或再灌注损伤的方法。