2-bromo-2-(4-fluorophenyl)acetamide | 251366-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-2-(4-fluorophenyl)acetamide
• 英文别名: 2-bromo-2-(p-fluorophenyl)acetamide；α-bromo-(4-fluorophenyl)acetamide
• CAS: 251366-32-2
• 化学式: C₈H₇BrFNO
• mdl: MFCD08444283
• 分子量: 232.052
• InChiKey: FDWUBKJXMHZBKT-UHFFFAOYSA-N

物化性质

• 熔点：
  112 °C
• 沸点：
  316.8±37.0 °C(Predicted)
• 密度：
  1.643±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-2-(4-fluorophenyl)acetamide 在 sodium hydroxide 、 盐酸羟胺 、 sodium acetate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 173.0h， 生成 2-amino-3-(4-fluorophenyl)-6-benzoylimidazo[1,2-b]pyridazine (Z)-oxime
  参考文献：
  名称：

  Imidazo[1,2-b]pyridazines, Novel Nucleus with Potent and Broad Spectrum Activity against Human Picornaviruses:  Design, Synthesis, and Biological Evaluation

  摘要：

  A novel structural class of picornavirus inhibitors comprising an imidazo[1,2-b]pyridazine nucleus was discovered. 2-Aminoimidazo[1,2-b]pyridazines (6d, (E/Z)-7b, (E)-7d, (Z)-7d, (El Z)-8b, (E)-10b, (E)-13a, (Z)-13a, (E)-13b, (Z)-13b, (E)-13c, and (Z)-13c) were designed and synthesized in an effort to identify potent broad spectrum antirhinoviral agents. A practical synthetic route to this chemical scaffold has been developed. The target compounds were evaluated in a plaque reduction assay and in a cytopathic effect assay. Our preliminary SAR studies highlight the minimum structural features required for antirhinovirus activity. Our data suggest that the nature of the linker between the phenyl and the imidazopyridazine moieties has a significant influence on the activity of these compounds. Oximes are slightly better than vinyl carboxamides at this position. The oximes are the most potent analogues against human rhinovirus 14 (HRV-14), and at the concentrations evaluated, no apparent cellular toxicity is noted. Furthermore, the E geometry appears to be a key element for activity; the Z isomer leads to a considerable loss in potency. Of particular interest, analogue 7b exhibits potent broad-spectrum antirhinoviral and antienteroviral activity when evaluated against a panel of seven additional rhino- and enteroviruses. The chemistry and the biological evaluations are discussed.

  DOI：

  10.1021/jm020583i
• 作为产物：
  描述：

  对氟苯乙酰氯 在 N-溴代丁二酰亚胺(NBS) 、 氨 作用下， 以 四氯化碳 、 正己烷 、 甲苯 为溶剂， 反应 7.0h， 生成 2-bromo-2-(4-fluorophenyl)acetamide
  参考文献：
  名称：

  Imidazo[1,2-b]pyridazines, Novel Nucleus with Potent and Broad Spectrum Activity against Human Picornaviruses:  Design, Synthesis, and Biological Evaluation

  摘要：

  A novel structural class of picornavirus inhibitors comprising an imidazo[1,2-b]pyridazine nucleus was discovered. 2-Aminoimidazo[1,2-b]pyridazines (6d, (E/Z)-7b, (E)-7d, (Z)-7d, (El Z)-8b, (E)-10b, (E)-13a, (Z)-13a, (E)-13b, (Z)-13b, (E)-13c, and (Z)-13c) were designed and synthesized in an effort to identify potent broad spectrum antirhinoviral agents. A practical synthetic route to this chemical scaffold has been developed. The target compounds were evaluated in a plaque reduction assay and in a cytopathic effect assay. Our preliminary SAR studies highlight the minimum structural features required for antirhinovirus activity. Our data suggest that the nature of the linker between the phenyl and the imidazopyridazine moieties has a significant influence on the activity of these compounds. Oximes are slightly better than vinyl carboxamides at this position. The oximes are the most potent analogues against human rhinovirus 14 (HRV-14), and at the concentrations evaluated, no apparent cellular toxicity is noted. Furthermore, the E geometry appears to be a key element for activity; the Z isomer leads to a considerable loss in potency. Of particular interest, analogue 7b exhibits potent broad-spectrum antirhinoviral and antienteroviral activity when evaluated against a panel of seven additional rhino- and enteroviruses. The chemistry and the biological evaluations are discussed.

  DOI：

  10.1021/jm020583i

文献信息

• PYRAZOLOQUINOLINES
  申请人：Fuchss Thomas

  公开号：US20130150359A1

  公开（公告）日：2013-06-13

  The invention relates to compounds of the formulae (I), (II) and (III), and/or physiologically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios. The compounds of the formula (I) can be used for the inhibition of serine/threonine protein kinases and for the sensitisation of cancer cells to anticancer agents and/or ionising radiation. The invention also relates to the use of the compounds of the formula (I) in the prophylaxis, therapy or progress control of cancer, tumours, metastases or angiogenesis disorders, in combination with radiotherapy and/or an anticancer agent. The invention furthermore relates to a process for the preparation of the compounds of the formula (I) by reaction of compounds of the formula (II) or (III) and optionally conversion of a base or acid of the compounds of the formula (I) into one of its salts

  该发明涉及化合物的结构式(I)、(II)和(III)，以及/或其生理上可接受的盐、互变异构体和立体异构体，包括所有比例的混合物。结构式(I)的化合物可用于抑制丝氨酸/苏氨酸蛋白激酶，并使癌细胞对抗癌药物和/或电离辐射敏感。该发明还涉及将结构式(I)的化合物与放疗和/或抗癌药物结合在一起，在预防、治疗或控制癌症、肿瘤、转移或血管生成障碍方面的应用。此外，该发明还涉及通过将结构式(II)或(III)的化合物反应，并可选地将结构式(I)的碱或酸转化为其盐之一的过程来制备结构式(I)的化合物。
• Anti-viral compounds
  申请人：Eli Lilly and Company

  公开号：US06358971B1

  公开（公告）日：2002-03-19

  The present invention relates to compounds of Formula (I) below, which inhibit the growth of picornaviruses, Hepatitus viruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus. wherein: A is phenyl, pyridyl, substituted phenyl, substituted pyridyl, or benzyl; R is hydrogen, COR4, or COCF3; X is N—OH, O, or CHR1; R1 is hydrogen, halo, CN, C1-C4 alkyl, —C≡CH, CO(C1-C4 alkyl), CO2(C1-C4 alkyl), or CONR2R3; R2 and R3 are independently hydrogen or C1-C4 alkyl; A′ is hydrogen, halo, C1-C6 alkyl, benzyl, naphthyl, thienyl, furyl, pyridyl, pyrollyl, COR4, S(O)nR4, or a group of the formula R4 is C1-C6 alkyl, phenyl, or substituted phenyl; n is 0, 1, or 2; R5 is independently at each occurrence hydrogen or halo; m is 1, 2, 3, or 4; and R6 is hydrogen, halo, CF3, OH, CO2H, NH2, NO2, CONHOCH3, C1-C4 alkyl, or CO2(C1-C4 alkyl), C1-C4 alkoxy; or a pharmaceutically acceptable salt thereof.

  本发明涉及以下化合物（I）的公式，它们抑制了小肠病毒、肝炎病毒、肠病毒、心病毒、脊髓灰质炎病毒、A组和B组柯萨奇病毒、回声病毒和门戈病毒的生长。其中：A为苯基、吡啶基、取代苯基、取代吡啶基或苄基；R为氢、COR4或COCF3；X为N—OH、O或CHR1；R1为氢、卤素、CN、C1-C4烷基、—C≡CH、CO（C1-C4烷基）、CO2（C1-C4烷基）或CONR2R3；R2和R3独立地为氢或C1-C4烷基；A′为氢、卤素、C1-C6烷基、苄基、萘基、噻吩基、呋喃基、吡啶基、吡咯基、COR4、S（O）nR4或R4的公式组，其中R4为C1-C6烷基、苯基或取代苯基；n为0、1或2；R5在每次出现时独立地为氢或卤素；m为1、2、3或4；以及R6为氢、卤素、三氟甲基、羟基、CO2H、NH2、NO2、CONHOCH3、C1-C4烷基、或CO2（C1-C4烷基）、C1-C4烷氧基；或其药用可接受盐。
• Pyrazoloquinolines
  申请人：Fuchss Thomas

  公开号：US08802712B2

  公开（公告）日：2014-08-12

  The invention relates to compounds of the formulae (I), (II) and (III), and/or physiologically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios. The compounds of the formula (I) can be used for the inhibition of serine/threonine protein kinases and for the sensitisation of cancer cells to anticancer agents and/or ionising radiation. The invention also relates to the use of the compounds of the formula (I) in the prophylaxis, therapy or progress control of cancer, tumours, metastases or angiogenesis disorders, in combination with radiotherapy and/or an anticancer agent. The invention furthermore relates to a process for the preparation of the compounds of the formula (I) by reaction of compounds of the formula (II) or (III) and optionally conversion of a base or acid of the compounds of the formula (I) into one of its salts

  本发明涉及式(I)、(II)和(III)的化合物及其生理上可接受的盐、互变异构体和立体异构体，包括所有比例的混合物。式(I)的化合物可用于抑制丝氨酸/苏氨酸蛋白激酶，并增强癌细胞对抗癌药物和/或电离辐射的敏感性。本发明还涉及将式(I)的化合物与放射治疗和/或抗癌药物结合在一起，用于预防、治疗或控制癌症、肿瘤、转移或血管生成障碍。本发明还涉及通过将式(II)或(III)的化合物反应，并将式(I)的化合物的碱或酸选项转化为其盐之一的方法来制备式(I)的化合物。
• Unusual Ring Closure Reaction of Amides with Pyrimidines: Novel Stereoselective Synthesis of Hexahydroimidazo[1,2-c]pyrimidines
  作者：Alberto Acero-Alarcón

  DOI：10.1055/s-1999-3640

  日期：1999.12
• ANTI-VIRAL COMPOUNDS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1077701A1

  公开（公告）日：2001-02-28