4-(bromomethyl)-5-(dibromomethyl)-1,3-thiazole | 185145-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(bromomethyl)-5-(dibromomethyl)-1,3-thiazole
• 英文别名: 4-(bromomethyl)-5-(dibromomethyl)thiazole；InChI=1/C5H4Br3NS/c6-1-3-4(5(7)8)10-2-9-3/h2,5H,1H
• CAS: 185145-58-8
• 化学式: C₅H₄Br₃NS
• 分子量: 349.871
• InChiKey: BZJZWPBZXCUOGB-UHFFFAOYSA-N

物化性质

• 沸点：
  340.2±37.0 °C(Predicted)
• 密度：
  2.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(bromomethyl)-5-(dibromomethyl)-1,3-thiazole 、 萘茜 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以70%的产率得到6,9-dihydroxyanthra[2,3-b]thiazole-5,10-dione
  参考文献：
  名称：

  Generation and Trapping of 4-Methylene-5-(bromomethylene)-4,5-dihydrothiazole with Dienophiles

  摘要：

  4-(Bromomethyl)-5-(dibromomethyl)thiazole (1) was prepared in good yields by bromination of 4,5-dimethylthiazole with 3.3 equiv of NBS in the presence of AIBN. Treatment of 1 with sodium iodide led to a thiazole o-quinodimethane 2 which was trapped in situ with dienophiles such as N-phenylmaleimide, DMAD, or acrylate derivatives. From the latter, 6-substituted-4,5-dihydrobenzothiazoles 7 are selectively formed. Anthra[2,3-b]thiazole-4,5-diones 13-15 were obtained from naphthoquinones. With 2- or 3-bromonaphthoquinones (11 or 12), the cycloadditions were found highly regioselective. Structural assignment of the regioisomers was made by a 2D H-1-C-13 HMBC technique performed on the aromatized cycloadduct 15b. Calculations of HOMO and LUMO frontier orbital coefficients by the semiempirical PM3 method show that the regiochemistry observed in the cycloadditions of 2 toward acrylate dienophiles or naphthoquinones 11 and 12 did not agree with the corresponding values.

  DOI：

  10.1021/jo961457n
• 作为产物：
  描述：

  4,5-二甲基噻唑 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 生成 4-(bromomethyl)-5-(dibromomethyl)-1,3-thiazole
  参考文献：
  名称：

  Hariri, Mouaffak Al; Galley, Olivier; Pautet, Felix, European Journal of Organic Chemistry, 1998, # 4, p. 593 - 594

  摘要：

  DOI：

文献信息

• Studies on quinones. Part 41: Synthesis and cytotoxicity of isoquinoline-containing polycyclic quinones☆
  作者：Jaime A. Valderrama、M. Florencia González、David Pessoa-Mahana、Ricardo A. Tapia、Houda Fillion、Felix Pautet、Jaime A. Rodriguez、Cristina Theoduloz、Guillermo Schmeda-Hirschmann

  DOI：10.1016/j.bmc.2006.03.008

  日期：2006.7.15

  new potentially anticancer drugs, isoquinolinequinone-containing polycyclic compounds have been designed and synthesized through highly regiocontrolled cycloaddition reactions of methyl 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate with polarized 1,3-dienes and a thiazole-o-quinodimethane. The new N-heterocyclic quinones were tested on normal human fibroblasts and four distinct human

  在寻找新的潜在抗癌药物中，已设计并通过高度区域控制的1,3-二甲基-5,8-二氧代-5,8-二氢异喹啉-4-羧酸甲酯与极化1的异环加成反应合成了含异喹啉醌的多环化合物。 ，3-二烯和噻唑-邻-喹二甲烷。在正常的人类成纤维细胞和四种不同的人类癌细胞系上测试了新的N-杂环醌。与参考药物依托泊苷相比，两种评估化合物显示出显着的体外活性（IC50：0.44-5.9 microM）。
• Synthesis and antiprotozoal evaluation of benzothiazolopyrroloquinoxalinones, analogues of kuanoniamine A
  作者：R Tapia

  DOI：10.1016/s0968-0896(03)00311-0

  日期：2003.8.5

  Boc-aminoethylindoloquinone 8, a key intermediate for the building of pentacyclic quinoneimines, analogues of kuanoniamine A, was synthesized by alkylation of 4,7-dimethoxyindole 3 with 1,2-dibromoethane followed by transformation into azide, reduction of the latter with trimethylphosphine in the presence of 2-(tert-butoxycarbonyloximino)-2-phenylacetonitrile and oxydative demethylation of the Boc-amine

  Boc-氨基乙基吲哚醌8，一种用于构建五环醌亚胺（关尼胺A类似物）的关键中间体，是通过将4,7-二甲氧基吲哚3与1,2-二溴乙烷进行烷基化，然后转化为叠氮化物，再用三甲基膦还原2-（叔丁氧基羰基肟基）-2-苯基乙腈的存在和Boc-胺6与氧化银（II）的氧化脱甲基作用。然后用噻唑邻喹啉甲烷10原位处理醌8，得到四环醌11的区域异构体混合物。用三氟乙酸和分子筛4-A处理该混合物，得到相应的醌亚胺12。进行区域异构体的分离。在硅胶上通过制备薄层色谱进行纯化。通过在极性较小的区域异构体12b上进行的2D 1H-13C HMBC相关进行结构分配。体外抗利什曼病测定表明，所测试的化合物对两种利什曼原虫具有良好的效力。以及针对弓形虫的强毒株，并且对THP-1细胞没有任何细胞毒性。
• Synthesis of novel pentacyclic pyrrolothiazolobenzoquinolinones, analogs of natural marine alkaloids
  作者：Valérie Bénéteau、Thierry Besson

  DOI：10.1016/s0040-4039(01)00258-1

  日期：2001.4

  Multistep synthesis (12 steps) of new pentacyclic compounds, which are structurally very close to natural marine alkaloids, was performed via a Diels-Alder reaction between 4-methylene-5-(bromomethylene)-4,5-dihydrothiazole and a protected dioxotryptamine, itself obtained from the commercially available 2,5-dimethoxybenzaldehyde. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and Antileishmanial Activity of Indoloquinones Containing a Fused Benzothiazole Ring
  作者：Ricardo A. Tapia、Yolanda Prieto、Félix Pautet、Monique Domard、Marie-Elizabeth Sarciron、Nadia Walchshofer、Houda Fillion

  DOI：10.1002/1099-0690(200212)2002:23<4005::aid-ejoc4005>3.0.co;2-l

  日期：2002.12
• Synthesis and antiprotozoal activity of naphthofuranquinones and naphthothiophenequinones containing a fused thiazole ring
  作者：Ricardo A. Tapia、Luz Alegria、Carlos D. Pessoa、Cristian Salas、Manuel J. Cortés、Jaime A. Valderrama、Marie-Elisabeth Sarciron、Félix Pautet、Nadia Walchshofer、Houda Fillion

  DOI：10.1016/s0968-0896(03)00122-6

  日期：2003.5

  The synthesis of tetracyclic quinones 10a,b, 14a,b, 19a,b and 20a,b is described. The preparations involve regioselective Diels-Alder reactions via trapping the thiazole o-quinodimethane 9 with several benzofuranquinones and benzothiophenequinones. The structure of the regioisomers was assigned through 2D NMR H-1-C-13 HMBC experiments performed on 10a and 14a. Compounds 10a,b, 14a as well as phenol I and the starting quinones 2, 5, 7 and 15 are evaluated against Leishmania sp., Toxoplasma gondii and THP-1 cells. Almost all the tested compounds exhibit significant antiprotozoal activities with lower cytotoxicities than the reference compounds. Among them, quitiones 2 and 14a possess the best activities towards L. donovani and T. gondii with the lowest toxicities. (C) 2003 Elsevier Science Ltd. All rights reserved.

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