2-(3,4-dichlorophenyl)-5-nitrobenzo[d]oxazole | 701254-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3,4-dichlorophenyl)-5-nitrobenzo[d]oxazole
• 英文别名: 2-(3,4-dichlorophenyl)-5-nitrobenzoxazole；2-(3,4-dichlorophenyl)-5-nitro-1,3-benzoxazole
• CAS: 701254-65-1
• 化学式: C₁₃H₆Cl₂N₂O₃
• 分子量: 309.108
• InChiKey: SGNNUTRXODICEO-UHFFFAOYSA-N

物化性质

• 沸点：
  438.5±40.0 °C(Predicted)
• 密度：
  1.540±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4-dichlorophenyl)-5-nitrobenzo[d]oxazole 在 铁粉 、 氯化铵 作用下， 以 industrial methylated spirit 、 水 为溶剂， 反应 1.75h， 以41%的产率得到2-(3,4-二氯-苯基)-苯并噁唑-5-胺
  参考文献：
  名称：

  Discovery of 2-Arylbenzoxazoles as Upregulators of Utrophin Production for the Treatment of Duchenne Muscular Dystrophy

  摘要：

  A series of novel 2-arylbenzoxazoles that upregulate the production of utrophin in murine H2K cells, as assessed using a luciferase reporter linked assay, have been identified. This compound class appears to hold considerable promise as a potential treatment for Duchenne muscular dystrophy. Following the delineation of structure-activity relationships in the series, a number of potent upregulators were identified, and preliminary ADME evaluation is described. These studies have resulted in the identification of 1, a compound that has been progressed to clinical trials.

  DOI：

  10.1021/jm200135z
• 作为产物：
  描述：

  3,4-二氯苯甲酰氯 、 2-氨基-4-硝基苯酚 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 2-(3,4-dichlorophenyl)-5-nitrobenzo[d]oxazole
  参考文献：
  名称：

  Novel anti-inflammatory and analgesic heterocyclic amidines that inhibit nitrogen oxide (NO) production

  摘要：

  含有抗炎和镇痛活性、抑制氮氧化物产生的杂环胺基化合物，化学式（I）如下：其中：G1和G2为氢、卤素、羟基、C1-C4烷氧基、C1-C4烷基和式为Q的胺基取代基，但对于化合物的每个化学式（I），G1或G2中仅有一个是式为Q的胺基取代基；其中取代基W、Y和X结合形成含有最多2个杂原子的同一环中的9-或10-成员双环杂芳衍生物；Z为芳基或杂芳基团、线性或支链状的C1-C6烷基或烯基链、C1-C4烷基-芳基团或C1-C4烷基-杂芳基团。

  公开号：

  US20050197331A1

文献信息

• Novel Anti-Inflammatory and Analgesic Heterocyclic Amidines that Inhibit Nitrogen Oxide (NO) Production
  申请人：MAKOVEC Francesco

  公开号：US20100120802A1

  公开（公告）日：2010-05-13

  Heterocyclic amidines with anti-inflammatory and analgesic activity that inhibit nitrogen oxide production, of formula (I): in which: G 1 and G 2 are hydrogen, halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, and an amidino substituent of formula Q, provided that, for each compound of formula (I), only one of the two substituents G 1 or G 2 is an amidino substituent of formula Q: and in which the substituents W, Y and X are combined to form 9- or 10-membered bicyclic heteroaromatic derivatives containing up to 2 hetero atoms in the same ring; and Z is an aryl or heteroaryl group, a linear or branched C 1 -C 6 alkyl or alkenyl chain, a C 1 -C 4 alkyl-aryl group or a C 1 -C 4 alkyl-heteroaryl group.

  具有抗炎和镇痛活性，能够抑制氮氧化物产生的杂环胺基化合物，化学式为（I）：其中：G1和G2是氢，卤素，羟基，C1-C4烷氧基，C1-C4烷基和公式Q的氨基甲基取代基，只有公式（I）中的两个取代基G1或G2中的一个是公式Q的氨基甲基取代基；其中取代基W，Y和X组合形成含有最多2个杂原子的9-或10成员双环杂芳基衍生物；Z是芳基或杂芳基基团，线性或分支的C1-C6烷基或烯基链，C1-C4烷基芳基基团或C1-C4烷基杂芳基基团。
• Anti-inflammatory and analgesic heterocyclic amidines that inhibit nitrogen oxide (NO) production
  申请人：Rottapharm S.p.A.

  公开号：US07674809B2

  公开（公告）日：2010-03-09

  Heterocyclic amidines with anti-inflammatory and analgesic activity that inhibit nitrogen oxide production, of formula (I): in which: G1 and G2 are hydrogen, halogen, hydroxyl, C1-C4 alkoxy, C1-C4 alkyl, and an amidino substituent of formula Q, provided that, for each compound of formula (I), only one of the two substituents G1 or G2 is an amidino substituent of formula Q: and in which the substituents W, Y and X are combined to form 9- or 10-membered bicyclic heteroaromatic derivatives containing up to 2 hetero atoms in the same ring; and Z is an aryl or heteroaryl group, a linear or branched C1-C6 alkyl or alkenyl chain, a C1-C4 alkyl-aryl group or a C1-C4 alkyl-heteroaryl group.

  具有抗炎和镇痛活性，抑制氮氧化物产生的杂环胺基的化合物，化学式（I）：其中：G1和G2是氢，卤素，羟基，C1-C4烷氧基，C1-C4烷基和式Q的胺基取代基，条件是对于化合物（I）中的每个化合物，只有G1或G2中的一个取代基是式Q的胺基取代基；其中取代基W，Y和X组合形成含有最多2个杂原子的9-或10成员双环杂芳衍生物；并且Z是芳基或杂芳基团，线性或支链C1-C6烷基或烯基链，C1-C4烷基芳基基团或C1-C4烷基杂芳基基团。
• US7674809B2
  申请人：——

  公开号：US7674809B2

  公开（公告）日：2010-03-09
• Novel anti-inflammatory and analgesic heterocyclic amidines that inhibit nitrogen oxide (NO) production
  申请人：Makovec Francesco

  公开号：US20050197331A1

  公开（公告）日：2005-09-08

  Heterocyclic amidines with anti-inflammatory and analgesic activity that inhibit nitrogen oxide production, of formula (I): in which: G 1 and G 2 are hydrogen, halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, and an amidino substituent of formula Q, provided that, for each compound of formula (I), only one of the two substituents G 1 or G 2 is an amidino substituent of formula Q: and in which the substituents W, Y and X are combined to form 9- or 10-membered bicyclic heteroaromatic derivatives containing up to 2 hetero atoms in the same ring; and Z is an aryl or heteroaryl group, a linear or branched C 1 -C 6 alkyl or alkenyl chain, a C 1 -C 4 alkyl-aryl group or a C 1 -C 4 alkyl-heteroaryl group.

  含有抗炎和镇痛活性、抑制氮氧化物产生的杂环胺基化合物，化学式（I）如下：其中：G1和G2为氢、卤素、羟基、C1-C4烷氧基、C1-C4烷基和式为Q的胺基取代基，但对于化合物的每个化学式（I），G1或G2中仅有一个是式为Q的胺基取代基；其中取代基W、Y和X结合形成含有最多2个杂原子的同一环中的9-或10-成员双环杂芳衍生物；Z为芳基或杂芳基团、线性或支链状的C1-C6烷基或烯基链、C1-C4烷基-芳基团或C1-C4烷基-杂芳基团。
• Discovery of 2-Arylbenzoxazoles as Upregulators of Utrophin Production for the Treatment of Duchenne Muscular Dystrophy
  作者：Daniel R. Chancellor、Kay E. Davies、Olivier De Moor、Colin R. Dorgan、Peter D. Johnson、Adam G. Lambert、Daniel Lawrence、Cristina Lecci、Carole Maillol、Penny J. Middleton、Gary Nugent、Séverine D. Poignant、Allyson C. Potter、Paul D. Price、Richard J. Pye、Richard Storer、Jonathon M. Tinsley、Renate van Well、Richard Vickers、Julia Vile、Fraser J. Wilkes、Francis X. Wilson、Stephen P. Wren、Graham M. Wynne

  DOI：10.1021/jm200135z

  日期：2011.5.12

  A series of novel 2-arylbenzoxazoles that upregulate the production of utrophin in murine H2K cells, as assessed using a luciferase reporter linked assay, have been identified. This compound class appears to hold considerable promise as a potential treatment for Duchenne muscular dystrophy. Following the delineation of structure-activity relationships in the series, a number of potent upregulators were identified, and preliminary ADME evaluation is described. These studies have resulted in the identification of 1, a compound that has been progressed to clinical trials.