2-氯-4,6-二吗啉-4-基-1,3,5-三嗪 | 7597-22-0

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 中文名称: 2-氯-4,6-二吗啉-4-基-1,3,5-三嗪
• 英文名称: 2-chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine
• 英文别名: 4,4'-(6-chloro-1,3,5-triazine-2,4-diyl)dimorpholine；2-chloro-4,6-dimorpholino-1,3,5-triazine；6-chloro-2,4-dimorpholino-1,3,5-triazine；4,4’-(6-chloro-1,3,5-triazine-2,4-diyl)dimorpholine；2-chloro-4,6-bis(morpholin-4-yl)-1,3,5-triazine；4,4′-(6-chloro-1,3,5-triazine-2,4-diyl)-dimorpholine；4-(4-chloro-6-morpholino-1,3,5-triazin-2-yl)morpholine；4-(4-chloro-6-morpholin-4-yl-1,3,5-triazin-2-yl)morpholine
• CAS: 7597-22-0
• 化学式: C₁₁H₁₆ClN₅O₂
• mdl: MFCD00432885
• 分子量: 285.733
• InChiKey: WYCCBNGHFYBVOM-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C
• 沸点：
  508.3±60.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.727
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 危险等级：
  IRRITANT
• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  2-氯-4,6-二吗啉-4-基-1,3,5-三嗪 在 sodium carbonate 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 potassium salt of 2-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) hydrazinecarbodithioic acid
  参考文献：
  名称：

  Asundaria, Shahrukh T.; Patel, Shreyas A.; Mehta, Kalpesh M., South African Journal of Chemistry, 2010, vol. 63, p. 141 - 144

  摘要：

  DOI：
• 作为产物：
  描述：

  三聚氯氰 生成 2-氯-4,6-二吗啉-4-基-1,3,5-三嗪
  参考文献：
  名称：

  COWPER, A. J.;TRIVEDI, G. S.;ASTIK, R. R.;THAKER, K. A., J. INST. CHEM., 1981, 53, N 2, 85-88

  摘要：

  DOI：

文献信息

• Synthesis of New Heteroaryl Substituted Morpholine Tagged Triazines and Evaluation of their Cytotoxic Activity
  作者：Sivaprasad Kasturi、Sujatha Surarapu、Srinivas Uppalanchi、Hasitha Shilpa Anantaraju、Shubham Dwivedi、Perumal Yogeeswari、Krishna S. Ethiraj、Jaya Shree Anireddy

  DOI：10.2174/1570180814666170605115335

  日期：2018.1.30

  Background: In the present study, new triazine derivatives 3, 4, 5, 6, 8 and 10 were synthesized starting from readily available cyanuric chloride 1 via nucleophilic displacement with morpholine followed by Suzuki or Stille coupling reactions and then the thermal displacement of chlorine atom with diverse substituted amines. Methods: All synthesized compounds were screened for their cytotoxic activity

  背景：在本研究中，新合成的三嗪衍生物3、4、5、6、8和10由容易获得的氰尿酰氯1经吗啉进行亲核取代，然后经Suzuki或Stille偶联反应，然后热取代氯原子而合成与各种取代的胺。 方法：筛选所有合成的化合物对HT-29，MDA-MB-231和HEK293细胞系的细胞毒活性。 结果与结论：化合物6a（HT50的IC50（µM）：0.32，MDA-MB-231为2.92）和化合物8c（IC50（µM）：HT-29为1.40，MDA-MB-231为1.60）。鉴定并与阿霉素和ZSTK474作参考标准进行比较。
• Compounds
  申请人：Hummersone Geoffrey Marc

  公开号：US20060199804A1

  公开（公告）日：2006-09-07

  Compounds of formula I: A-B-C  (I) and isomers, salts, solvates, chemically protected forms, and prodrugs thereof wherein: B is selected from the group consisting of: where R N is H or Me; or B is a divalent C 5 heterocyclic residue containing one or two ring heteroatoms; A is: R A3 and R A5 are independently selected from halo, OR O and R AC , where R O is H or Me, and R AC is H or C 1-4 alkyl; X A is selected from N and CR A4 , where R A4 is selected from H, OR O , CH 2 OH, CO 2 H, NHSO 2 Me and NHCOMe; R A2 and R A6 are independently selected from H, halo and OR O ; or R A3 and R A4 together with the carbon atoms to which they are attached, or RA2 and R A3 together with the carbon atoms to which they are attached, may form a C 5-6 heterocylic or heteroaromatic ring, containing at least one nitrogen ring atom; where if X is not N, 1, 2, or 3 of R A2 to R A6 are not H; C is: where X is selected from N and CH, Y is selected from N and CH, and Z is selected from N and CR C6 ; R C3 is selected from H, halo and an optionally substituted N-containing C 5-7 heterocyclic group; R C5 is a group selected from: which group may be selected by one or two C 1-4 alkyl groups or a carboxy group; R C6 is H; or, when X and Y are N, R C5 and R C6 (when Z is CR C6 ) together with the carbon atoms to which they are attached may form a fused C 6 aromatic ring selected from the group consisting of:

  化合物的化学式I： A-B-C  (I) 及其异构体、盐、溶剂合物、化学保护形式和前药，其中： B选自以下组合： 其中R N 为H或Me； 或B是含有一个或两个环异原子的二价C 5 杂环残基； A为： R A3 和R A5 独立选择自卤、OR O 和R AC ，其中R O 为H或Me，R AC 为H或C 1-4 烷基； X A 选自N和CR A4 ，其中R A4 选自H、OR O 、CH 2 OH、CO 2 H、NHSO 2 Me和NHCOMe； R A2 和R A6 独立选择自H、卤素和OR O ； 或R A3 和R A4 与它们连接的碳原子一起，或RA2和R A3 与它们连接的碳原子一起，可形成含有至少一个氮环原子的C 5-6 杂环或杂芳环； 如果X不是N，则R A2 至R A6 中的1、2或3个不是H； C为： 其中X选自N和CH，Y选自N和CH，Z选自N和CR C6 ； R C3 选自H、卤素和可选择性取代的含氮C 5-7 杂环基； R C5 为以下组合之一： 该组合可由一个或两个C 1-4 烷基或一个羧基选择； R C6 为H； 或者，当X和Y为N时，R C5 和R C6 （当Z为CR C6 时）与它们连接的碳原子可形成所选自的融合C 6 芳香环之一：
• 신규 하이드록사메이트 유도체 및 이를 포함하는 암의 예방 또는 치료용 약제학적 조성물
  申请人：HANMI PHARM. CO., LTD. 한미약품 주식회사(120100356638) Corp. No ▼ 134811-0197550BRN ▼124-87-00613

  公开号：KR20160038598A

  公开（公告）日：2016-04-07

  본 발명은 신규한 하이드록사메이트 유도체 또는 이의 약학적으로 허용 가능한 염, 및 이를 활성성분으로 함유하는 암의 예방 또는 치료용 약제학적 조성물에 관한 것이다. 본 발명에서 제공하는 신규 하이드록사메이트 유도체 또는 이의 약학적으로 허용 가능한 염은 세포 내 DNA 팩킹 구조를 제어하는 신호전달에 관여하는 히스톤 디아세틸라제-3(Histone Deacetylase-3)를 선택적으로 억제하여 기존의 pan-HDAc 억제제의 독성적 한계를 해결하면서, 암세포의 성장을 효과적으로 억제할 수 있다.

  本发明涉及一种新的羟基甲酰胺衍生物或其药学上可接受的盐，以及含有其作为活性成分的用于预防或治疗癌症的药学组合物。本发明提供的新羟基甲酰胺衍生物或其药学上可接受的盐通过选择性抑制参与细胞内DNA包装结构调控的信号传导的组蛋白去乙酰化酶-3（Histone Deacetylase-3），可以有效抑制癌细胞的生长，同时解决传统泛HDAc抑制剂的毒性限制。
• Discovery of a Novel HDAC3 Selective Inhibitor and its Evaluation in Lymphoma Model
  作者：Chang-Ju Choi、Mira Kim、Sun Young Han、Jiyoung Jeon、Jae Ho Lee、Jeong-In Oh、Kwee Hyun Suh、Dong-Churl Suh、Kwang-Ok Lee

  DOI：10.1002/bkcs.10619

  日期：2016.1

  HDAC inhibitors are in clinical development stages for the treatment of cancer as well as immune and inflammatory disorders. Although there are several approved HDAC inhibitors by the US FDA, they show a broad inhibitory spectrum against HDAC subfamily. Herein, we synthesized a series of novel hydroxamate analogs, and evaluated them with lymphoma cancer cell. Conclusively, we identified an HDAC3 selective

  组蛋白脱乙酰基酶（HDAC）抑制是潜在的有吸引力的癌症治疗方法。许多HDAC抑制剂正处于临床开发阶段，用于治疗癌症以及免疫和炎性疾病。尽管有几种获得美国FDA批准的HDAC抑制剂，但它们显示出对HDAC亚家族的广泛抑制谱。在这里，我们合成了一系列新型异羟肟酸酯类似物，并用淋巴瘤癌细胞对其进行了评估。最终，我们确定了HDAC3选择性抑制剂，该抑制剂对淋巴瘤模型显示出良好的抗癌活性，并具有良好的药物代谢和药代动力学（DMPK）特性。
• Synthesis, Spectra, and Theoretical Investigations of 1,3,5-Triazines Compounds as Ultraviolet Rays Absorber Based on Time-Dependent Density Functional Calculations and three-Dimensional Quantitative Structure-Property Relationship
  作者：Xueding Wang、Yilian Xu、Lu Yang、Xiang Lu、Hao Zou、Weiqing Yang、Yuanyuan Zhang、Zicheng Li、Menglin Ma

  DOI：10.1007/s10895-018-2235-2

  日期：2018.3

  A series of 1,3,5-triazines were synthesized and their UV absorption properties were tested. The computational chemistry methods were used to construct quantitative structure-property relationship (QSPR), which was used to computer aided design of new 1,3,5-triazines ultraviolet rays absorber compounds. The experimental UV absorption data are in good agreement with those predicted data using the Time-dependent

  合成了一系列1,3,5-三嗪，并测试了它们的紫外线吸收性能。利用计算化学方法构建了定量的结构-性质关系（QSPR），并将其用于新型1,3,5-三嗪紫外线吸收剂化合物的计算机辅助设计。实验性紫外线吸收数据与使用时变密度泛函理论（TD-DFT）[B3LYP / 6–311 + G（d，p）]的预测数据非常吻合。合适的预测模型（R  > 0.8，P <0.0001）。利用Sybyl程序的多重拟合分子比对规则，建立了可预测的三维定量结构-性质关系（3D-QSPR）模型，该结论与TD-DFT计算吻合。对这种紫外线吸收剂化合物的异常光稳定性机理进行了研究，并证实其主要归因于它们通过超快激发态质子转移（ESIPT）进行激发态失活的能力。1,3,5-三嗪化合物的分子内氢键（IMHB）是激发态质子转移的基础，已通过红外光谱，紫外光谱，不同构象异构体的结构和能量方面以及前沿分子轨道分析进行了探索。