2-mercapto-4,5-bis<3,4-(methylenedioxy)phenyl>imidazole | 66660-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-mercapto-4,5-bis<3,4-(methylenedioxy)phenyl>imidazole
• 英文别名: 4,5-bis(3,4-methylenedioxyphenyl)-2-mercaptoimidazole；2-mercapto-4,5-bis[3,4-(methylenedioxy)phenyl]imidazole；4,5-bis(1,3-benzodioxol-5-yl)-1,3-dihydroimidazole-2-thione
• CAS: 66660-00-2
• 化学式: C₁₇H₁₂N₂O₄S
• 分子量: 340.359
• InChiKey: OQBQGLWXHMQGEN-UHFFFAOYSA-N

物化性质

• 熔点：
  282-283 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  515.7±60.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-mercapto-4,5-bis<3,4-(methylenedioxy)phenyl>imidazole 、 1,2-二溴乙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以56%的产率得到5,6-Bis-benzo[1,3]dioxol-5-yl-2,3-dihydro-imidazo[2,1-b]thiazole
  参考文献：
  名称：

  5,6-Diaryl-2,3-dihydroimidazo[2,1-b]thiazoles: a new class of immunoregulatory antiinflammatory agents

  摘要：

  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.

  DOI：

  10.1021/jm00147a008
• 作为产物：
  描述：

  4,5-bis<3,4-(methylenedioxy)phenyl>imidazole 在 sulfur 作用下， 以 环丁砜 为溶剂， 反应 2.0h， 以4.0 g的产率得到2-mercapto-4,5-bis<3,4-(methylenedioxy)phenyl>imidazole
  参考文献：
  名称：

  4,5-二芳基-2-（取代硫代）-1H-咪唑及其亚砜和砜的制备及其抗关节炎和止痛作用。

  摘要：

  合成了一系列的4,5-二芳基-2-（取代硫代）-1H-咪唑，并在大鼠佐剂诱导的关节炎试验和小鼠苯基-对苯醌扭曲（PQW）试验中用作抗炎和镇痛药。发现几种类似物比苯基丁a和消炎痛更有效。讨论了构效关系。发现其中一种化合物4,5-双（4-氟苯基）-2-[（（1,1,2,2-四氟乙基）-磺酰基] -1H-咪唑（8d，tiflamizole）是在大鼠佐剂诱导的关节炎试验中具有消炎痛的作用，目前正在作为抗关节炎药进行临床试验。

  DOI：

  10.1021/jm00147a011

文献信息

• 5,6-Phenyl-2,3-dihydroimidazo [2,1-b] thiazoles
  申请人：SmithKline Corporation

  公开号：US04263311A1

  公开（公告）日：1981-04-21

  The compounds are 5,6-phenyl-2,3-dihydroimidazo[2,1-b]thiazoles which have antiarthritic activity. A preferred compound is 5,6-bis(p-anisyl)-2,3-dihydroimidazo[2,1-b]thiazole.

  这些化合物是5,6-苯基-2,3-二氢咪唑[2,1-b]噻唑的衍生物，具有抗关节炎活性。其中一种优选化合物是5,6-双对甲氧基苯基-2,3-二氢咪唑[2,1-b]噻唑。
• Bis-imidazoles, their preparation and pharmaceutical compositions containing them
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0010361A1

  公开（公告）日：1980-04-30

  The use is disclosed of compounds of the formula (I):- where R' is methoxy, methylthio, trifluoromethyl, chloro, fluoro or bromo; R2 is hydrogen or with R1 is methylenedioxy; R3 is hydrogen or methyl; n is 0, 1 or 2; andX is -(CH2)m- where m is 0 to 4, 1,2-propanediyl, 1,3-propan-2 -oldiyl or 1,3-propan -2-onediyl and their pharmaceutically acceptable salts, provided that m is not 0 when R1 is chloro, as anti-arthritic agents. Also disclosed are pharmaceutical compositions comprising a compound of formula (I) as defined above or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier. Some compounds of formula (I) are novel, such compounds have formula (I) where R' is methoxy, methylthio, trifluro-methyl, chloro, fluoro or brom; R2 is hydrogen or with R1 is methylenedioxy; R3 is hydrogen or methyl; n is 0, 1 or2; and X is -(CH2)m- where m is 0 to 4, 1,2-propanediyl, 1,3-propan-2 -oldiyl or 1,3-propan-2-onediyl, and pharmaceutically acceptable salts, provided that when R1 is chlorom is not 0 and when R1 is methoxy and n is 0 m is not 2. A process is disclosed for the preparation of these novel compounds.

  本发明公开了式(I)化合物的用途 其中 R'是甲氧基、甲硫基、三氟甲基、氯、氟或溴；R2 是氢或与 R1 一起是亚甲基二氧基；R3 是氢或甲基；n 是 0、1 或 2；和 X 是-(CH2)m-（其中 m 为 0 至 4）、1,2-丙二基、1,3-丙-2-烯二基或 1,3-丙-2-壬二基及其药学上可接受的盐，条件是当 R1 为氯时，m 不为 0，作为抗关节炎剂。还公开了药物组合物，其中包含如上定义的式 (I) 化合物或其药学上可接受的盐以及药学上可接受的载体。 一些式 (I) 的化合物是新型的，此类化合物具有式 (I) 其中 R' 是甲氧基、甲硫基、三氟甲基、氯、氟或溴；R2 是氢或与 R1 一起是亚甲基二氧基；R3 是氢或甲基；n 是 0、1 或 2；和 X 是-(CH2)m-（其中 m 为 0 至 4）、1,2-丙二基、1,3-丙-2-烯二基或 1,3-丙-2-壬二基，以及药学上可接受的盐，条件是当 R1 为氯时，m 不为 0，当 R1 为甲氧基且 n 为 0 时，m 不为 2。本发明公开了制备这些新型化合物的工艺。
• Yoshida et al., Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1951, vol. 54, p. 685
  作者：Yoshida et al.

  DOI：——

  日期：——
• BENDER, P. E.;HILL, D. T.;OFFEN, P. H.;RAZGAITIS, K.;LAVANCHY, P.;STRINGE+, J. MED. CHEM., 1985, 28, N 9, 1169-1177
  作者：BENDER, P. E.、HILL, D. T.、OFFEN, P. H.、RAZGAITIS, K.、LAVANCHY, P.、STRINGE+

  DOI：——

  日期：——
• SHARPE, T. R.;CHERKOFSKY, S. C.;HEWES, W. E.;SMITH, D. H.;GREGORY, W. A.;+, J. MED. CHEM., 1985, 28, N 9, 1188-1194
  作者：SHARPE, T. R.、CHERKOFSKY, S. C.、HEWES, W. E.、SMITH, D. H.、GREGORY, W. A.、+

  DOI：——

  日期：——