5-chloro-1,3-dihydroxyacridone | 273943-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-chloro-1,3-dihydroxyacridone
• 英文别名: 5-Chloro-1,3-dihydroxy-10H-acridin-9-one
• CAS: 273943-69-4
• 化学式: C₁₃H₈ClNO₃
• 分子量: 261.664
• InChiKey: FNIGHIXUKIHUMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-1,3-dihydroxyacridone 、 碘甲烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以70%的产率得到5-Chloro-1-hydroxy-3-methoxy-10-methyl-10H-acridin-9-one
  参考文献：
  名称：

  Anti-Herpes Simplex Virus Activity of Substituted 1-Hydroxyacridones

  摘要：

  5-Chloro-1,3-dihydroxyacridone, 1, is a potent and selective inhibitor of Herpes Simplex Virus Type-1 (HSV-1).(1) Substituted 1,3-dihydroxyacridones represent a new class of nonnucleoside HSV-1 inhibitors, and biochemical studies indicate a novel mechanism of action for 1, although the target is not yet defined.(2) With the goal of lead optimization, analogues of 1 were synthesized in an effort to describe the structure-activity relationships between 1 and its hypothetical binding site. Modifications of key functional groups led to the identity of several features of I that were important for activity. In the process, a more expedient and reliable synthesis of 1 and its analogues was developed. Analogues were evaluated against HSV-1 and HSV-2 using a viral plaque-elimination assay for viral inhibition of HSV-1 and HSV-2, and effects on replication of the host cell were also measured in order to assess a therapeutic index (TI) of selectivity. Several new analogues with significant antiviral activity were identified, including 5-methoxy-1,3-dihydroxyacridone (11), which inhibits replication of several HSV-2 strains with a mean ED50 of 0.7 muM and a TI range of 25-60-fold.

  DOI：

  10.1021/jm030206l
• 作为产物：
  描述：

  间苯三酚 、 2-氨基-3-氯苯甲酸 反应 0.67h， 以32%的产率得到5-chloro-1,3-dihydroxyacridone
  参考文献：
  名称：

  Anti-Herpes Simplex Virus Activity of Substituted 1-Hydroxyacridones

  摘要：

  5-Chloro-1,3-dihydroxyacridone, 1, is a potent and selective inhibitor of Herpes Simplex Virus Type-1 (HSV-1).(1) Substituted 1,3-dihydroxyacridones represent a new class of nonnucleoside HSV-1 inhibitors, and biochemical studies indicate a novel mechanism of action for 1, although the target is not yet defined.(2) With the goal of lead optimization, analogues of 1 were synthesized in an effort to describe the structure-activity relationships between 1 and its hypothetical binding site. Modifications of key functional groups led to the identity of several features of I that were important for activity. In the process, a more expedient and reliable synthesis of 1 and its analogues was developed. Analogues were evaluated against HSV-1 and HSV-2 using a viral plaque-elimination assay for viral inhibition of HSV-1 and HSV-2, and effects on replication of the host cell were also measured in order to assess a therapeutic index (TI) of selectivity. Several new analogues with significant antiviral activity were identified, including 5-methoxy-1,3-dihydroxyacridone (11), which inhibits replication of several HSV-2 strains with a mean ED50 of 0.7 muM and a TI range of 25-60-fold.

  DOI：

  10.1021/jm030206l

文献信息

• Light absorbing compounds for optical polymers
  申请人：Bausch & Lomb Incorporated

  公开号：US09249249B2

  公开（公告）日：2016-02-02

  An optical polymeric material that can substantially block the transmission of ultraviolet light as well as selected portion of violet light. The polymeric material will include monomeric units of one or more lens monomers, and monomeric units of a monomer of formula (I).

  一种光学聚合物材料，可以实质性地阻挡紫外线以及选定部分紫外光的传输。该聚合物材料将包括一个或多个透镜单体的单体单元，以及公式（I）的单体单元。
• Ophthalmic devices containing UV blocker and methods for their preparation
  申请人：Bausch & Lomb Incorporated

  公开号：US11066530B2

  公开（公告）日：2021-07-20

  A method for preparing an ophthalmic device containing an ultraviolet (UV) blocker is disclosed. The method involves (a) soaking an ophthalmic device in one or more first solvent solutions to swell the ophthalmic device; (b) soaking the swelled ophthalmic device in one or more second solvents solutions comprising a UV blocker to de-swell the ophthalmic device and entrap the UV blocker in the ophthalmic device, wherein the UV blocker is a benzotriazole and (c) sterilizing the de-swelled ophthalmic device.

  本发明公开了一种制备含有紫外线（UV）阻隔剂的眼科装置的方法。该方法包括：(a) 将眼科装置浸泡在一种或多种第一溶剂溶液中，使眼科装置膨胀；(b) 将膨胀的眼科装置浸泡在一种或多种包含紫外线阻断剂的第二溶剂溶液中，使眼科装置脱泡并将紫外线阻断剂夹带在眼科装置中，其中紫外线阻断剂为苯并三唑；(c) 对脱泡的眼科装置进行灭菌。
• LIGHT ABSORBING COMPOUNDS FOR OPTICAL POLYMERS
  申请人：Bausch & Lomb Incorporated

  公开号：EP2875091B1

  公开（公告）日：2016-11-16
• US9249249B2
  申请人：——

  公开号：US9249249B2

  公开（公告）日：2016-02-02
• Anti-Herpes Simplex Virus Activity of Substituted 1-Hydroxyacridones
  作者：Christopher T. Lowden、Kenneth F. Bastow

  DOI：10.1021/jm030206l

  日期：2003.11.1

  5-Chloro-1,3-dihydroxyacridone, 1, is a potent and selective inhibitor of Herpes Simplex Virus Type-1 (HSV-1).(1) Substituted 1,3-dihydroxyacridones represent a new class of nonnucleoside HSV-1 inhibitors, and biochemical studies indicate a novel mechanism of action for 1, although the target is not yet defined.(2) With the goal of lead optimization, analogues of 1 were synthesized in an effort to describe the structure-activity relationships between 1 and its hypothetical binding site. Modifications of key functional groups led to the identity of several features of I that were important for activity. In the process, a more expedient and reliable synthesis of 1 and its analogues was developed. Analogues were evaluated against HSV-1 and HSV-2 using a viral plaque-elimination assay for viral inhibition of HSV-1 and HSV-2, and effects on replication of the host cell were also measured in order to assess a therapeutic index (TI) of selectivity. Several new analogues with significant antiviral activity were identified, including 5-methoxy-1,3-dihydroxyacridone (11), which inhibits replication of several HSV-2 strains with a mean ED50 of 0.7 muM and a TI range of 25-60-fold.