4,4-diethyl-1-methyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one | 850198-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 4,4-diethyl-1-methyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one
• 英文别名: 4,4-diethyl-1-methyl-6-nitro-3,1-benzoxazin-2-one
• CAS: 850198-49-1
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: XCGJYLXHTTYIID-UHFFFAOYSA-N

物化性质

• 沸点：
  385.4±42.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4-diethyl-1-methyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one 在 5%-palladium/activated carbon sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以81%的产率得到6-amino-4,4-diethyl-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one
  参考文献：
  名称：

  6-Amino-1,4-dihydro-benzo[d][1,3] oxazin-2-ones and analogs useful as progesterone receptor modulators

  摘要：

  提供具有公式I结构的化合物。在公式I中，R1为H，OH，取代或未取代的C1至C3烷基，C1至C3全氟烷基，或COR6；R6为H，取代或未取代的C1至C4烷基，芳基，取代或未取代的C1至C4甲氧基，取代或未取代的C1至C3氨基烷基；R2和R3为H，取代或未取代的C1至C6烷基，C1至C6全氟烷基，取代或未取代的C2至C6烯基，取代或未取代的C2至C6炔基，取代或未取代的C3至C6环烷基，取代或未取代的芳基，或取代或未取代的杂环；或者R2和R3融合形成螺环；R4为NHR7，OR7，NHSO2R7，或OSO2R7；Q为O，S，NR8，或CR9R10；或其药用可接受的盐，酯或前药。这些化合物可用作孕激素受体调节剂，并用于治疗与孕激素受体相关的疾病。

  公开号：

  US20050085470A1
• 作为产物：
  描述：

  1-(2-氨基-苯基)-丙烷-1-酮 在 硫酸 、 亚硝酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 4,4-diethyl-1-methyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one
  参考文献：
  名称：

  SAR studies of 6-(arylamino)-4,4-disubstituted-1-methyl-1,4-dihydro-benzo[d][1,3]oxazin-2-ones as progesterone receptor antagonists

  摘要：

  We previously disclosed that 6-aryl benzoxazin-2-ones were PR modulators. In a continuation of this work we examined the SAR of new 6-arylamino benzoxazinones and found the targets 1-25, with an extra amino linker between the pendent 6-aryl groups and benzoxazinone or benzoxazine-2-thione core, were PR antagonists. A series of compounds with substituents at the 1- and 4-positions as well as different 6-aryl groups were prepared and tested in the T47D cell alkaline phosphatase assay. Interestingly, the SAR unveiled from the 6-arylamino benzoxazinones was quite different from those of their parent compounds. For example, in contrast to the 6-aryl benzoxazinones, methyl substitution at the 1-position significantly increased the potency of 6-arylamino benzoxazinones. Several 6-arylamino benzoxazinones (e.g., 12, IC50 = 5.0 nM) had low nanomolar in vitro potency as PR antagonists in the T47D cell alkaline phosphatase assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.060

文献信息

• 6-Amino-1,4-dihydro-benzo[d][1,3] oxazin-2-ones and analogs useful as progesterone receptor modulators
  申请人：Zhang Puwen

  公开号：US20050085470A1

  公开（公告）日：2005-04-21

  Compounds having the structure of formula I are provided. In formula I, R 1 is H, OH, substituted or unsubstituted C 1 to C 3 alkyl, C 1 to C 3 perfluoroalkyl, or COR 6 ; R 6 is H, substituted or unsubstituted C 1 to C 4 alkyl, aryl, substituted or unsubstituted C 1 to C 4 alkoxy, substituted or unsubstituted C 1 to C 3 aminoalkyl; R 2 and R 3 are H, substituted or unsubstituted C 1 to C 6 alkyl, C 1 to C 6 perfluoroalkyl, substituted or unsubstituted C 2 to C 6 alkenyl, substituted or unsubstituted C 2 to C 6 alkynyl, substituted or unsubstituted C 3 to C 6 cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic; or R 2 and R 3 are fused to form spirocyclic rings; R 4 is NHR 7 , OR 7 , NHSO 2 R 7 , or OSO 2 R 7 ; Q is O, S, NR 8 , or CR 9 R 10 ; or a pharmaceutically acceptable salt, ester, or prodrug thereof. Such compounds are useful as progesterone receptor modulators and for treating progesterone receptor related conditions.

  提供具有公式I结构的化合物。在公式I中，R1为H，OH，取代或未取代的C1至C3烷基，C1至C3全氟烷基，或COR6；R6为H，取代或未取代的C1至C4烷基，芳基，取代或未取代的C1至C4甲氧基，取代或未取代的C1至C3氨基烷基；R2和R3为H，取代或未取代的C1至C6烷基，C1至C6全氟烷基，取代或未取代的C2至C6烯基，取代或未取代的C2至C6炔基，取代或未取代的C3至C6环烷基，取代或未取代的芳基，或取代或未取代的杂环；或者R2和R3融合形成螺环；R4为NHR7，OR7，NHSO2R7，或OSO2R7；Q为O，S，NR8，或CR9R10；或其药用可接受的盐，酯或前药。这些化合物可用作孕激素受体调节剂，并用于治疗与孕激素受体相关的疾病。
• 6-Amino-1,4-dihydro-benzo[d][1,3]oxazin-2-ones and analogs useful as progesterone receptor modulators
  申请人：Zhang Puwen

  公开号：US20070225281A1

  公开（公告）日：2007-09-27

  Compounds having the structure of formula I are provided. In formula I, R 1 is H, OH, substituted or unsubstituted C 1 to C 3 alkyl, C 1 to C 3 perfluoroalkyl, or COR 6 ; R 6 is H, substituted or unsubstituted C 1 to C 4 alkyl, aryl, substituted or unsubstituted C 1 to C 4 alkoxy, substituted or unsubstituted C 1 to C 3 aminoalkyl; R 2 and R 3 are H, substituted or unsubstituted C 1 to C 6 alkyl, C 1 to C 6 perfluoroalkyl, substituted or unsubstituted C 2 to C 6 alkenyl, substituted or unsubstituted C 2 to C 6 alkynyl, substituted or unsubstituted C 3 to C 6 cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic; or R 2 and R 3 are fused to form spirocyclic rings; R 4 is NHR 7 , OR 7 , NHSO 2 R 7 , or OSO 2 R 7 ; Q is O, S, NR 8 , or CR 9 R 10 ; or a pharmaceutically acceptable salt, ester, or prodrug thereof. Such compounds are useful as progesterone receptor modulators and for treating progesterone receptor related conditions.

  提供了具有式I结构的化合物。在式I中，R1是H、OH、取代或未取代的C1到C3烷基、C1到C3全氟烷基或COR6；R6是H、取代或未取代的C1到C4烷基、芳基、取代或未取代的C1到C4甲氧基、取代或未取代的C1到C3氨基烷基；R2和R3是H、取代或未取代的C1到C6烷基、C1到C6全氟烷基、取代或未取代的C2到C6烯基、取代或未取代的C2到C6炔基、取代或未取代的C3到C6环烷基、取代或未取代的芳基或取代或未取代的杂环基；或R2和R3融合形成螺环；R4是NHR7、OR7、NHSO2R7或OSO2R7；Q是O、S、NR8或CR9R10；或其药学上可接受的盐、酯或前药。这些化合物可用作孕激素受体调节剂，并用于治疗孕激素受体相关疾病。
• 6-amino-1,4-dihydro-benzo[d][1,3] oxazin-2-ones and analogs useful as progesterone receptor modulators
  申请人：Wyeth

  公开号：US07247625B2

  公开（公告）日：2007-07-24

  Compounds having the structure of formula I are provided. In formula I, R1 is H, OH, substituted or unsubstituted C1 to C3 alkyl, C1 to C3 perfluoroalkyl, or COR6; R6 is H, substituted or unsubstituted C1 to C4 alkyl, aryl, substituted or unsubstituted C1 to C4 alkoxy, substituted or unsubstituted C1 to C3 aminoalkyl; R2 and R3 are H, substituted or unsubstituted C1 to C6 alkyl, C1 to C6 perfluoroalkyl, substituted or unsubstituted C2 to C6 alkenyl, substituted or unsubstituted C2 to C6 alkynyl, substituted or unsubstituted C3 to C6 cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic; or R2 and R3 are fused to form spirocyclic rings; R4 is NHR7, OR7, NHSO2R7, or OSO2R7; Q is O, S, NR8, or CR9R10; or a pharmaceutically acceptable salt, ester, or prodrug thereof. Such compounds are useful as progesterone receptor modulators and for treating progesterone receptor related conditions.

  提供了具有公式I结构的化合物。在公式I中，R1是H，OH，取代或未取代的C1到C3烷基，C1到C3全氟烷基或COR6; R6是H，取代或未取代的C1到C4烷基，芳基，取代或未取代的C1到C4烷氧基，取代或未取代的C1到C3氨基烷基; R2和R3是H，取代或未取代的C1到C6烷基，C1到C6全氟烷基，取代或未取代的C2到C6烯基，取代或未取代的C2到C6炔基，取代或未取代的C3到C6环烷基，取代或未取代的芳基或取代或未取代的杂环基; 或R2和R3融合形成螺环; R4是NHR7，OR7，NHSO2R7或OSO2R7; Q是O，S，NR8或CR9R10; 或其药学上可接受的盐，酯或前药。这些化合物可用作孕激素受体调节剂，并用于治疗孕激素受体相关疾病。
• 6-amino-1,4-dihydro-benzo[d][1,3]oxazin-2-ones and analogs useful as progesterone receptor modulators
  申请人：Wyeth

  公开号：US07354915B2

  公开（公告）日：2008-04-08

  Compounds having the structure of formula I are provided. In formula I, R1 is H, OH, substituted or unsubstituted C1 to C3 alkyl, C1 to C3 perfluoroalkyl, or COR6; R6 is H, substituted or unsubstituted C1 to C4 alkyl, aryl, substituted or unsubstituted C1 to C4 alkoxy, substituted or unsubstituted C1 to C3 aminoalkyl; R2 and R3 are H, substituted or unsubstituted C1 to C6 alkyl, C1 to C6 perfluoroalkyl, substituted or unsubstituted C2 to C6 alkenyl, substituted or unsubstituted C2 to C6 alkynyl, substituted or unsubstituted C3 to C6 cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic; or R2 and R3 are fused to form spirocyclic rings; R4 is NHR7, OR7, NHSO2R7, or OSO2R7; Q is O, S, NR8, or CR9R10; or a pharmaceutically acceptable salt, ester, or prodrug thereof. Such compounds are useful as progesterone receptor modulators and for treating progesterone receptor related conditions

  提供了具有公式I结构的化合物。在公式I中，R1是H，OH，取代或未取代的C1至C3烷基，C1至C3全氟烷基或COR6; R6是H，取代或未取代的C1至C4烷基，芳基，取代或未取代的C1至C4烷氧基，取代或未取代的C1至C3氨基烷基; R2和R3是H，取代或未取代的C1至C6烷基，C1至C6全氟烷基，取代或未取代的C2至C6烯基，取代或未取代的C2至C6炔基，取代或未取代的C3至C6环烷基，取代或未取代的芳基，或取代或未取代的杂环基; 或者R2和R3融合形成螺环状环; R4是NHR7，OR7，NHSO2R7或OSO2R7; Q是O，S，NR8或CR9R10; 或其药学上可接受的盐，酯或前药。这些化合物可用作孕激素受体调节剂，并用于治疗孕激素受体相关疾病。
• US7247625B2
  申请人：——

  公开号：US7247625B2

  公开（公告）日：2007-07-24