3,4-diphenyl-6,7-dihydro-imidazo[2,1-b][1,3]thiazole | 24736-19-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,4-diphenyl-6,7-dihydro-imidazo[2,1-b][1,3]thiazole
• 英文别名: 5,6-diphenyl-2,3-dihydroimidazo[2,1-b][1,3]thiazole；5,6-diphenyl-2,3-dihydro-imidazo[2,1-b]thiazole；5,6-Diphenyl-imidazo<2,1-b>thiazolin
• CAS: 24736-19-4
• 化学式: C₁₇H₁₄N₂S
• 分子量: 278.378
• InChiKey: LPJBOYDHVYYELT-UHFFFAOYSA-N

物化性质

• 熔点：
  232-234 °C(Solv: ethanol (64-17-5))
• 沸点：
  469.3±48.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-diphenyl-6,7-dihydro-imidazo[2,1-b][1,3]thiazole 生成 5,6-diphenyl-2,3-dihydroimidazo[2,1-b][1,3]thiazole 1-oxide
  参考文献：
  名称：

  DAVIS, LOUISA LAM;CHENG, HUNG-YUAN, ABSTR. PAP. 194TH ACS NAT. MEET. (AMER. CHEM. SOC.), NEW ORLEANS, LA, AUG+

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[(2-hydroxyeth-1-yl)thio]-4,5-diphenyl-1H-imidazole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.1h， 以78%的产率得到3,4-diphenyl-6,7-dihydro-imidazo[2,1-b][1,3]thiazole
  参考文献：
  名称：

  Novel Regioselective Hydroxyl-Alkylation of 4,5-Diphenylimidazole-2-Thione and A Competitive Intramolecular Ring Closure of the S-Hydroxyalkyl-Imidazoles to Imidazo[2,1-b]Thiazines and Thiazoles. Role of Catalyst, Microwave Irradiation, and Solid Support

  摘要：

  Under both conventional method (CM) and microwave (MW) irradiation (MWI) conditions, alkylation of 4,5-diphenylimidazole-2-thione (1) with halogeno-alkanols 2 or 5, chloroglycerol 11 and 2,3-O-isopropylidene-1-O-(p-tolylsulfonyl)-glycerol (8) in presence of sodium ethoxide or sodium acetate in alcohol afforded regioselectively the corresponding S-alkylated analogues 3, 6, 9, and 12; they also were obtained using MW in absence and presence of bentonite as solid support with no change in regioselectivity. In the presence of potassium carbonate in DMF, the bisalkylated analogues 4, 7, 10, and 13 were obtained except in case of compound 13 where it was accompanied with the imidazothiazine 14. A convenient approach for imidazo-[2,1-b] thiazines and thiazoles 14 - 16 could be achieved by intramolecular dehydrative ring closure of the S-hydroxyalkylated imidazoles 3, 6, and 12 using potassium carbonate in DMF under both conventional and microwave methods. Isopropylidenation of 12 and 13 and deprotection of 9 and 10 also were investigated.

  DOI：

  10.1080/15257770701426179

文献信息

• Synthesis of some 3,4-disubstituted-6,7-dihydro-imidazo[2,1-b][1,3]thiazole and 3,4-disubstituted-7,8-dihydro-6H-imidazo[2,1-b][1,3]thiazine derivatives and evaluation of their cytotoxicities against F2408 and 5RP7 cells
  作者：Asiye Meriç、Zerrin İncesu、İbrahim Hatipoğlu

  DOI：10.1007/s00044-008-9090-7

  日期：2008.4

  This article describes the synthesis of 3,4-disubstituted-6,7-dihydro-imidazo[2,1-b][1,3]thiazoles and 3,4-disubstituted-7,8-dihydro-6H-imidazo[2,1-b][1,3]thiazines, having substituted or nonsubstituted phenyl rings at the 5,6 and 2,3 positions, respectively, their cytotoxic effects through noncancer (F2408) and cancer (5RP7) cells, and their detailed 1H- and 13C-nuclear magnetic resonance (NMR) spectral

  本文介绍了3,4-二取代-6,7-二氢咪唑并[2,1-b] [1,3]噻唑和3,4-二取代-7,8-二氢-6H-咪唑并[2]的合成，1-b] [1,3]噻嗪类化合物，分别在5,6和2,3位具有取代或未取代的苯环，它们通过非癌细胞（F2408）和癌细胞（5RP7）的细胞毒性作用，及其详细信息1 H和13 C核磁共振（NMR）光谱表征。在碳酸钾（K 2 CO 3）存在下，通过将4,5-二芳基-咪唑-2-硫酮和二卤代烷烃（即1,2-二卤代乙烷或1,3-二卤代丙烷）环化获得标题化合物。在 N，N -二甲基甲酰胺（DMF）。4，5-二芳基-咪唑-2-硫酮是通过将α-羟基酮（酰基辅酶）缩合而制得的，而α-羟基酮是通过将氰化物用醛处理醛与硫脲在AcOH中缩合而制得的。咪唑并[2,1-b] [1,3]噻唑和咪唑并[2,1-b] [1,3]噻嗪衍生物的结构已通过红外（IR），1 H-NMR和13 C-确证。
• 5,6-Diaryl-2,3-dihydroimidazo[2,1-b]thiazoles: a new class of immunoregulatory antiinflammatory agents
  作者：Paul E. Bender、David Hill、Priscilla H. Offen、Kazys Razgaitis、Patricia Lavanchy、Orum D. Stringer、Blaine M. Sutton、Don E. Griswold、Michael DiMartino

  DOI：10.1021/jm00147a008

  日期：1985.9

  A series of substituted 5,6-diaryl-2,3-dihydroimidazo[2,1-b]thiazoles were synthesized and evaluated in the rat adjuvant-induced arthritis and mouse oxazolone-induced contact sensitivity assays to determine the potential of these compounds for use as immunoregulatory antiinflammatory agents. This class of compounds was derived by combining salient structural features of the antiinflammatory agent flumizole and the immunoregulatory drug levamisole. Unlike the latter two, a number of compounds in the target series were found to possess the desired combination of activities. Exploration of structure-activity relationships in the adjuvant-induced arthritic rat assay revealed that optimal potency was exhibited by symmetrically substituted 5,6-diaryl compounds having one of the following alkyl heteroatom or halogen functions at the para position: methoxy, ethoxy, methylthio, N-ethyl-N-methylamino, fluoro, or chloro. Scrambling of these two substituent classes to yield the asymmetrically substituted 5,6-diaryl compounds resulted in potent activity only with the 5-alkyl heteroatom, 6-halo-substituted regioisomers. However in the oxazolone-induced contact sensitivity assay, no consistent relationship of variation in activity with structural change was apparent. The initial target compound 5,6-bis(4-methoxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole (1) was compared with its progenitors in additional models of inflammation and immunoregulation.
• Mohan,J. et al., Indian Journal of Chemistry, 1973, vol. 11, p. 747 - 749
  作者：Mohan,J. et al.

  DOI：——

  日期：——
• Synthesis of 2,3-dihydro-and 2,3,5,6-tetrahydro derivatives of imidazo(2,1-B)-thiazole
  作者：I. A. Mazur、P. M. Kochergin、V. I. Fomenko

  DOI：10.1007/bf00832994

  日期：1969.8
• DOU H. J.-M.; LUDWIKOW M.; HASSANALY P.; KISTER J.; METZGER J., J. HETEROCYCL. CHEM., 1980, 17, NO 2, 393-395
  作者：DOU H. J.-M.、 LUDWIKOW M.、 HASSANALY P.、 KISTER J.、 METZGER J.

  DOI：——

  日期：——