4-(氯甲基)-6-吗啉-4-基-1,3,5-噻嗪-2-胺 | 21868-41-7

• 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: 4-(氯甲基)-6-吗啉-4-基-1,3,5-噻嗪-2-胺
• 中文别名: 2-氨基-4-氯甲基-6-N-吗啉基-1,3,5-三嗪；2-氨基-4-(氯甲基)-6-N-吗啉基-S-三嗪；S-三嗪,2-氨基-4-(氯甲基)-6-N-吗啉基-；4-(氯甲基)-6-(4-吗啉)-1,3,5-三嗪-2-胺；4-(氯甲基)-6-N-吗啉基-1,3,5-三嗪-2-胺；4-(氯甲基)-6-吗啉-4-基-1,3,5-三嗪-2-胺；4-(氯甲基)-6-(4- 吗啉)-1,3,5-三嗪-2-胺；[4-(氯甲基)-6-N-吗啉基-S-三嗪-2-基]胺
• 英文名称: 2-amino-4-morpholino-6-chloromethyl-1,3,5-triazine
• 英文别名: 4-Amino-6-morpholino-2-chlormethyl-1,3,5-triazin；4-chloromethyl-6-morpholin-4-yl-[1,3,5]triazin-2-ylamine；4-(Chloromethyl)-6-morpholin-4-yl-1,3,5-triazin-2-amine
• CAS: 21868-41-7
• 化学式: C₈H₁₂ClN₅O
• mdl: MFCD01679202
• 分子量: 229.669
• InChiKey: MFAGDEITRDZSFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-(氯甲基)-6-吗啉-4-基-1,3,5-噻嗪-2-胺 、 N-苯基哌嗪 生成 4-morpholin-4-yl-6-(4-phenyl-piperazin-1-ylmethyl)-[1,3,5]triazin-2-ylamine
  参考文献：
  名称：

  Das,P.C. et al., Indian Journal of Chemistry, 1968, vol. 6, p. 691 - 693

  摘要：

  DOI：
• 作为产物：
  描述：

  吗啉胍 、 氯乙酸乙酯 以 乙醇 为溶剂， 反应 12.0h， 以51%的产率得到4-(氯甲基)-6-吗啉-4-基-1,3,5-噻嗪-2-胺
  参考文献：
  名称：

  新型2,4-二氨基-1,3,5-三嗪衍生物的合成，结构表征和抗肿瘤活性。

  摘要：

  描述了合成，基于NMR的结构解析和8的X射线分析以及新型2,4-二氨基-1,3,5-三嗪衍生物5和7-22的抗肿瘤活性。在NCI上进行的筛选显示，大多数衍生物在0.148-56.2 microM浓度的各种肿瘤细胞系上具有中等至强的生长抑制活性。2-Amino-6-bromomethyl-4-（3,5,5-trimethyl-2-pyrazoline）-1,3,5-triazine 11显示出最有效的抗肿瘤活性，其平均中点值为log（10）GI50，所有测试的log（10）TGI50和log（10）LC50分别等于-5.26，-4.81和-4.37，因此，可以将其视为抗癌剂进一步开发的先导结构。

  DOI：

  10.1016/s0223-5234(00)01194-6

文献信息

• Studies on Antitumor Substances. VIII. Syntheses of 4-Amino-6-substituted Amino-2-substituted sym-Triazine Derivatives
  作者：SEIGORO HAYASHI、MITSURU FURUKAWA、YOKO FUJINO、SHIGEKI YOSHIMATSU

  DOI：10.1248/cpb.17.329

  日期：——

  In order to synthesize a variety of 4-amino-6-substituted amino-2-substituted symtriazine, 1-substituted biguanide was allowed to react with ethyl chloroacetate to give 4-amino-6-substituted amino-2-chloromethyl-sym-triazine, from which the purpose compounds were derived. The reactions of 4-amino-6-substituted amino-2-chloromethyl-symtriazine with amines and alkylthiols were successfully carried out to give 4-amino-6-substituted amino-2-substituted aminomethyl-sym-triazine and 4-amino-6-substituted amino-2-alkylthiomethyl-sym-triazine, respectively. However, in the reaction with sodium alkanethiosulfonate, it was found to result in the formation of the corresponding sulfone afforded by the partial desulfurization in the intermediately formed 4-amino-6-substituted amino-2-methoxythiosulfonyl-sym-triazine. This sulfone was confirmed to be identical with that obtained by oxidation of the corresponding sulfide. The mercaptylation of 4-amino-6-piperidino-2-chloromethyl-sym-triazine with thiourea was resulted in the formation of the corresponding disulfide rather than the thiol compound anticipated.

  为了合成多种4-氨基-6-取代氨基-2-取代对称三嗪，1-取代双脲与氯乙酸乙酯反应，生成4-氨基-6-取代氨基-2-氯甲基对称三嗪，从中衍生出目标化合物。4-氨基-6-取代氨基-2-氯甲基对称三嗪与胺及烷基硫醇的反应成功进行，分别生成4-氨基-6-取代氨基-2-取代氨基甲基对称三嗪和4-氨基-6-取代氨基-2-烷基硫甲基对称三嗪。然而，在与烷基硫酸钠的反应中，发现形成了相应的磺酮，这是由于部分脱硫在中间生成的4-氨基-6-取代氨基-2-甲氧基硫代磺酸基对称三嗪中发生的。这种磺酮被确认与通过氧化相应的硫化物获得的磺酮相同。4-氨基-6-哌啶基-2-氯甲基对称三嗪与硫脲的反应形成了相应的二硫化物，而不是预期的硫醇化合物。
• Carbonic anhydrase inhibitors. Regioselective synthesis of novel series 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides and their inhibition of the human cytosolic isozymes I and II and transmembrane cancer-associated isozymes IX and XII
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Daniela Vullo、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2012.08.006

  日期：2012.10

  A series of novel 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides 4-6, 9-17 and 21-31 have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA.EC 4.2.1.1), that is the cytosolic CA I and II, and cancer-associated isozymes CA IX and XII. Against the human isozymes hCA I the new compounds showed K(I)s in the range of 224-4830 nM, whereas toward hCA II, K(I)s = 318-873 nM. Isozyme hCA IX was inhibited with K(I)s = 11.8-93.4 nM, and hCA XII with 23.5 -82.3 nM. Compounds 12-14, 27 and 29-31 have an activity against hCA I (K(I)s = 224-889 nM) which is comparable to the clinically used sulfonamide DCP (K(I)s = 1200 nM). Several of new compounds, including 9, 10, 21, 24, 26-28 and 30 have an activity against hCA IX (K(I)s = 11.8-38.6 nM) which is comparable or more effective than the clinically used sulfonamides AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). Compounds 9, 10, 13, 21-23, 26 and 27 were also very effective hCA XII inhibitors, with inhibition constants ranged from 23.5 to 47.2 nM comparable or more effective than sulfonamides EZA (K(I)s = 22 nM) or DCP (K(I)s = 50 nM), respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.
• ——
  作者：V. I. Kelarev、M. A. Silin、O. A. Borisova

  DOI：10.1023/a:1025102300933

  日期：——
• Das,P.C. et al., Indian Journal of Chemistry, 1970, vol. 8, p. 590 - 592
  作者：Das,P.C. et al.

  DOI：——

  日期：——
• Synthesis, structural characterization and antitumor activity of novel 2,4-diamino-1,3,5-triazine derivatives
  作者：Z. Brzozowski、F. Sączewski、M. Gdaniec

  DOI：10.1016/s0223-5234(00)01194-6

  日期：2000.12

  The syntheses, structural elucidation based on NMR spectroscopy and X-ray analysis of 8 as well as antitumor activities of novel 2,4-diamino-1,3,5-triazine derivatives 5 and 7-22 are described. Screenings performed at NCI showed that most derivatives possessed a moderate to strong growth inhibition activity on various tumor panel cell lines between 0.148 and 56.2 microM concentrations. 2-Amino-6-bromomethyl-4-(3

  描述了合成，基于NMR的结构解析和8的X射线分析以及新型2,4-二氨基-1,3,5-三嗪衍生物5和7-22的抗肿瘤活性。在NCI上进行的筛选显示，大多数衍生物在0.148-56.2 microM浓度的各种肿瘤细胞系上具有中等至强的生长抑制活性。2-Amino-6-bromomethyl-4-（3,5,5-trimethyl-2-pyrazoline）-1,3,5-triazine 11显示出最有效的抗肿瘤活性，其平均中点值为log（10）GI50，所有测试的log（10）TGI50和log（10）LC50分别等于-5.26，-4.81和-4.37，因此，可以将其视为抗癌剂进一步开发的先导结构。

表征谱图