bis(3-fluoro-4-methoxy)desoxybenzoin | 1827-54-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: bis(3-fluoro-4-methoxy)desoxybenzoin
• 英文别名: 3,3'-difluoro-4,4'-dimethoxy-deoxybenzoin；3,3'-Difluor-4,4'-dimethoxy-desoxybenzoin；3'-fluoro-2-(3-fluoro-4-methoxyphenyl)-4'-methoxyacetophenone；m,m'-Difluordesoxyanisoin；1,2-bis(3-fluoro-4-methoxyphenyl)ethanone
• CAS: 1827-54-9
• 化学式: C₁₆H₁₄F₂O₃
• 分子量: 292.282
• InChiKey: SMIXCMBLNFEUSS-UHFFFAOYSA-N

物化性质

• 熔点：
  149-150 °C(Solv: methanol (67-56-1))
• 沸点：
  200-220 °C(Press: 6 Torr)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis(3-fluoro-4-methoxy)desoxybenzoin 在 溴 、 potassium carbonate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 19.0h， 生成 5,6-bis-(3-fluoro-4-methoxy-phenyl)-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：

  3-氟-4-甲氧基苯甲醛 在 盐酸 、 potassium cyanide 、 tin 、 copper(II) sulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 生成 bis(3-fluoro-4-methoxy)desoxybenzoin
  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

文献信息

• Pyridazine compounds and compositions containing the same
  申请人：Kowa Co., Ltd.

  公开号：US06348468B1

  公开（公告）日：2002-02-19

  This invention relates to pyridazine derivatives represented by the formula (1): wherein R1 represents a (substituted) aryl group, R2 represents a phenyl group substituted at 4-position by a lower alkoxyl group or a lower alkylthio group, R3 represents a lower alkoxyl group, a halogenated lower alkyl group, a lower cycloalkyl group, a (subsituted) aryl group, a (substituted) aryloxy group, a (substituted) nitrogen-containing heterocyclic ring residue, a (substituted) aminocarbonyl group or a lower alkylcarbonyl group, A represents a single bond, a lower alkylene group or a lower alkenylene group, X represents O or S, and the dashed line indicates that the carbon-carbon bond between the 4-position and the 5-position is a single bond or a double bond, or salts thereof; and also to medicines containing them as effective ingredients. These compounds have excellent inhibitory activity against interleukin-1&bgr; production, and are useful as preventives and therapeutics for immune system diseases, inflammatory diseases, ischemic diseases and the like.

  这项发明涉及由式（1）表示的吡啶嗪衍生物： 其中R1代表（取代的）芳基，R2代表在4位被低烷氧基或低烷硫基取代的苯基，R3代表低烷氧基、卤代低烷基、低环烷基、（取代的）芳基、（取代的）芳氧基、（取代的）含氮杂环环残基、（取代的）氨基羰基或低烷基羰基，A代表单键、低烷基烯基或低烷烯基，X代表O或S，虚线表示4位和5位之间的碳-碳键为单键或双键，或其盐；以及含有它们作为有效成分的药物。这些化合物对白细胞介素-1β的产生具有出色的抑制活性，并可用作免疫系统疾病、炎症性疾病、缺血性疾病等的预防和治疗药物。
• Novel pyridazine derivatives and medicines containing the same as effective ingredients
  申请人：Ohkuchi Masao

  公开号：US20050267113A1

  公开（公告）日：2005-12-01

  This invention relates to pyridazine derivatives represented by the formula (1): wherein R 1 represents a (substituted) aryl group, R 2 represents a phenyl group substituted at 4 -position by a lower alkoxyl group or a lower alkylthio group, R 3 represents a lower alkoxyl group, a halogenated lower alkyl group, a lower cycloalkyl group, a (subsituted) aryl group, a (substituted) aryloxy group, a (substituted) nitrogen-containing heterocyclic ring residue, a (substituted) aminocarbonyl group or a lower alkylcarbonyl group, A represents a single bond, a lower alkylene group or a lower alkenylene group, X represents O or S, and the dashed line indicates that the carbon-carbon bond between the 4 -position and the 5 -position is a single bond or a double bond, or salts thereof; and also to medicines containing them as effective ingredients. These compounds have excellent inhibitory activity against interleukin- 1 β production, and are useful as preventives and therapeutics for immmune system diseases, inflammatory diseases, ischemic diseases and the like.

  本发明涉及由式（1）表示的吡嗪衍生物：其中R1表示（取代）芳基基团，R2表示在4-位被低烷氧基基团或低烷硫基基团取代的苯基基团，R3表示低烷氧基基团、卤代低烷基基团、低环烷基基团、（取代）芳基基团、（取代）芳氧基基团、（取代）含氮杂环环残基、（取代）氨基甲酰基或低烷基甲酰基，A表示单键、低烷基亚ethylene基或低烷基亚烯基，X表示O或S，虚线表示4-位和5-位之间的碳-碳键为单键或双键，或其盐；以及包含它们作为有效成分的药物。这些化合物对白细胞介素-1β的产生有出色的抑制活性，并且可用作免疫系统疾病、炎症性疾病、缺血性疾病等的预防和治疗。
• NOVEL PYRIDAZINE DERIVATIVES AND MEDICINES CONTAINING THE SAME AS EFFECTIVE INGREDIENTS
  申请人：OHKUCHI Masao

  公开号：US20090270399A1

  公开（公告）日：2009-10-29

  This invention relates to pyridazine derivatives represented by the formula (1): wherein R 1 represents a (substituted) aryl group, R 2 represents a phenyl group substituted at 4-position by a lower alkoxyl, group or a lower alkylthio group, R 3 represents a lower alkoxyl group, a halogenated lower alkyl group, a lower cycloalkyl group, a (substituted) aryl group, a (substituted) aryloxy group, a (substituted) nitrogen-containing heterocyclic ring residue, a (substituted) aminocarbonyl group or a lower alkylcarbonyl group, A represents a single bond, a lower alkylene group or a lower alkenylene group, X represents O or S, and the dashed line indicates that the carbon-carbon bond between the 4-position and the 5-position is a single bond or a double bond, or salts thereof; and also to medicines containing them as effective ingredients. These compounds have excellent inhibitory activity against interleukin-1β production, and are useful as preventives and therapeutics for immune system diseases, inflammatory diseases, ischemic diseases and the like.

  本发明涉及由式（1）表示的吡嗪衍生物： 其中R1表示（取代的）芳基基团，R2表示在4位被低烷氧基团或低烷硫基团取代的苯基基团，R3表示低烷氧基团、卤代的低烷基团、低环烷基团、（取代的）芳基基团、（取代的）芳氧基基团、（取代的）含氮杂环环残基、（取代的）氨基甲酰基团或低烷基甲酰基团，A表示单键、低烷基烷基或低烯基烷基，X表示O或S，虚线表示4位和5位之间的碳-碳键为单键或双键，或其盐；以及含有它们作为有效成分的药物。这些化合物具有优异的抑制白细胞介素-1β产生的活性，可用作预防和治疗免疫系统疾病、炎症性疾病、缺血性疾病等。
• NOVEL PYRIDAZINE DERIVATIVES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：Kowa Co., Ltd.

  公开号：EP1043317A1

  公开（公告）日：2000-10-11

  This invention relates to pyridazine derivatives represented by the formula (1): wherein R1 represents a (substituted) aryl group, R2 represents a phenyl group substituted at 4-position by a lower alkoxyl group or a lower alkylthio group, R3 represents a lower alkoxyl group, a halogenated lower alkyl group, a lower cycloalkyl group, a (subsituted) aryl group, a (substituted) aryloxy group, a (substituted) nitrogen-containing heterocyclic ring residue, a (substituted) aminocarbonyl group or a lower alkylcarbonyl group, A represents a single bond, a lower alkylene group or a lower alkenylene group, X represents O or S, and the dashed line indicates that the carbon-carbon bond between the 4-position and the 5-position is a single bond or a double bond, or salts thereof; and also to medicines containing them as effective ingredients. These compounds have excellent inhibitory activity against interleukin-1β production, and are useful as preventives and therapeutics for immune system diseases, inflammatory diseases, ischemic diseases and the like.

  本发明涉及式（1）所代表的哒嗪衍生物： 其中 R1 代表（取代的）芳基，R2 代表在 4 位被低级烷氧基或低级烷硫基取代的苯基，R3 代表低级烷氧基、卤代低级烷基、低级环烷基、（取代的）芳基、（取代的）芳氧基、（取代的）含氮杂环残基、一个（取代的）氨基羰基或一个低级烷基羰基，A 代表单键、一个低级亚烷基或一个低级亚烯基，X 代表 O 或 S，虚线表示 4 位和 5 位之间的碳-碳键是单键或双键，或其盐；以及含有这些化合物作为有效成分的药物。这些化合物对白细胞介素-1β的产生具有良好的抑制活性，可作为免疫系统疾病、炎症性疾病、缺血性疾病等的预防和治疗药物。
• Pyridazine derivatives and medicines containing the same as effective ingredients
  申请人：Kowa Co., Ltd.

  公开号：EP2017266A1

  公开（公告）日：2009-01-21

  A pyridazine derivative represented by the following formula (1): wherein R1 represents a phenyl or pyridyl group which may be substituted by 1 to 3 substituents selected from a halogen atom and a C1-6 alkoxyl group, R2 represents a phenyl group substituted at least at 4-position by a C1-6 alkoxyl group, C1-6 alkylthio group, a C1-6 alkylsulfinyl group, or a C1-6 alkylsulfonyl group, and optionally has one or more substituents at the other position by 1 or 2 substituents selected from a halogen atom, a C1-6alkoxyl group, C1-6 alkylthio group, a C1-6 alkylsulfinyl group, or a C1-6 alkylsulfonyl group, R3 represents a C1-6 alkoxyl group, a fluorinated C1-6 alkyl group, C1-6 alkyl group or a C3-8 cycloalkyl group, A represents a single bond or linear or branched C1-6 alkylene group or C2-9 alkenylene group, X represents an oxygen atom or a sulfur atom; or a salt thereof.

  下式(1)所代表的哒嗪衍生物： 其中 R1 代表苯基或吡啶基，可被 1 至 3 个选自卤素原子和 C1-6 烷氧基的取代基取代、 R2 代表至少在 4 位被 C1-6 烷氧基、C1-6 烷硫基、C1-6 烷基亚磺酰基或 C1-6 烷基磺酰基取代的苯基，并可选择在另一位置被 1 或 2 个选自卤素原子、C1-6 烷氧基、C1-6 烷硫基、C1-6 烷基亚磺酰基或 C1-6 烷基磺酰基的取代基取代、 R3 代表 C1-6 烷氧基、氟化 C1-6 烷基、C1-6 烷基或 C3-8 环烷基、 A 代表单键或直链或支链 C1-6 烯基或 C2-9 烯基、 X 代表氧原子或硫原子； 或其盐。