ethyl 5-[(Bromoacetyl)amino]-3-phenyl-2H-pyrido[4,3-b][1,4]oxazin-7-ylcarbamate | 86970-63-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 5-[(Bromoacetyl)amino]-3-phenyl-2H-pyrido[4,3-b][1,4]oxazin-7-ylcarbamate
• 英文别名: ethyl {5-[(bromoacetyl)amino]-3-phenyl-2H-pyrido[4,3-d][1,4]oxazin-7-yl}carbamate；Carbamic acid, (5-((bromoacetyl)amino)-3-phenyl-2H-pyrido(4,3-b)-1,4-oxazin-7-yl)-, ethyl ester；ethyl N-[5-[(2-bromoacetyl)amino]-3-phenyl-2H-pyrido[4,3-b][1,4]oxazin-7-yl]carbamate
• CAS: 86970-63-0
• 化学式: C₁₈H₁₇BrN₄O₄
• 分子量: 433.261
• InChiKey: JFADYGIDHJWJTB-UHFFFAOYSA-N

物化性质

• 熔点：
  >230 °C
• 沸点：
  574.8±50.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl (5,6-diamino-4-hydroxypyridin-2-yl)carbamate hydrochloride 在 potassium acetate 、 溶剂黄146 作用下， 反应 26.0h， 生成 ethyl 5-[(Bromoacetyl)amino]-3-phenyl-2H-pyrido[4,3-b][1,4]oxazin-7-ylcarbamate
  参考文献：
  名称：

  合成潜在的抗癌药。吡啶并[4,3-b] [1,4]恶嗪和吡啶并[4,3-b] [1,4]噻嗪。

  摘要：

  （6-氨基-4-氯-5-硝基吡啶-2-基氨基甲酸乙酯）（3）的甲酸与甲酸的水解，得到相应的4-羟基吡啶4。4的硝基的催化氢化得到5 -氨基-4-羟基吡啶5，在室温下与α-卤代酮在乙酸中反应，得到一系列3-和2,3-取代的乙基（5-氨基-2H-吡啶[4,3-b ] [1,4]恶嗪-7-基）氨基甲酸酯8.用热的浓盐酸处理8，再生吡啶合成子5.在3与硫代乙酸酯的反应中，产物进行水解和空气氧化，得到相应的二硫键6.同时还原6的硝基和二硫键得到5-氨基-4-巯基吡啶7将其与α-卤代酮在室温下于乙酸中或在乙醇和水的混合物中在回流下反应，得到一系列3-，2,3-和2,2,3-取代的乙基（5-氨基-2H-吡啶并[4,3-b] [1,4]噻嗪-7-基）氨基甲酸酯9.这些吡啶并恶嗪和吡啶并噻嗪对培养的L1210细胞增殖和有丝分裂指数以及小鼠存活的影响确定患有P388白血病。

  DOI：

  10.1021/jm00365a012

文献信息

• Pyrido[4,3-b][1,4]oxazines and pyrido[4,3-b][1,4]thiazines
  申请人：Southern Research Institute

  公开号：US04451650A1

  公开（公告）日：1984-05-29

  There are disclosed certain 2H-pyrido[4,3-b][1,4]oxazines and 2H-pyrido[4,3-b][1,4]thiazines which possess biological activity. The compounds have the structure: ##STR1## wherein n has a value of 1,2 or 3; X is oxygen or sulfur; R.sub.1 is a lower alkyl group, e.g., an alkyl group containing up to six carbon atoms such as methyl, ethyl, propyl, butyl, etc.; R.sub.2 is a member selected from the group consisting of hydrogen, alkyl radicals having from about one to about 12 carbon atoms, preferably from about one to about six carbon atoms; alkenyl radicals having from about two to about 15 carbon atoms; preferably from about two to about 10 carbon atoms; cycloalkyl radicals having from about three to about 20 carbon atoms, preferably from about three to about 15 carbon atoms; aryl, aralkyl and alkaryl radicals having from about six to about 20 carbon atoms, preferably from about six to about 15 carbon atoms; a halogen radical, e.g., chlorine, fluorine, bromine and iodine; a hydroxyl group; an amino group; an alkoxy or aryloxy group; a carboxyl group or an alkylcarboxyl group having from about one to about 10 carbon atoms, preferably from about one to about five carbon atoms; an alkythio group or an arylthio group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a sulfonic acid group or alkyl- or arylsulfonyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or arylsulfinyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or aryl mono- or diamino group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a hydrocarbyl group, such as defined above, carrying halogen, hydroxyl, amino, alkoxy or aryloxy; when taken together with the aromatic ring to which it is attached, a fused ring structure such as naphthyl; and, when taken together with R.sub.3, an alkylene radical containing from about one to about 12 carbon atoms, preferably from about one to about six carbon atoms; R.sub.3 is hydrogen, methyl, phenyl or, when taken with R.sub.2, an alkylene radical as previously defined; R.sub.4 is hydrogen or methyl; R.sub.3 and R.sub.4, when taken together are the radical .dbd.0; and R.sub.5 and R.sub.6 are both hydrogen, or one is hydrogen and the other is the radical ##STR2## or where taken together are the radical .dbd.CHN(CH.sub.3).sub.2.

  已披露了某些具有生物活性的2H-吡啶并[4,3-b][1,4]噁唑和2H-吡啶并[4,3-b][1,4]噻唑。这些化合物具有以下结构：其中n的值为1、2或3；X为氧或硫；R.sub.1是一个较低的烷基基团，例如，一个含有最多六个碳原子的烷基基团，如甲基、乙基、丙基、丁基等；R.sub.2是从氢、具有约1到约12个碳原子的烷基基团（最好从约1到约6个碳原子）、具有约2到约15个碳原子的烯基基团（最好从约2到约10个碳原子）、具有约3到约20个碳原子的环烷基基团（最好从约3到约15个碳原子）、约6到约20个碳原子的芳基、芳基烷基和烷基基团（最好从约6到约15个碳原子）、卤素基团，例如氯、氟、溴和碘；羟基；氨基；烷氧基或芳基氧基；羧基或具有约1到约10个碳原子的烷基羧基，最好从约1到约5个碳原子；硫代烷基基团或硫代芳基基团，具有约1到约20个碳原子，最好从约1到约15个碳原子；磺酸基团或具有约1到约20个碳原子的烷基或芳基磺酰基团，最好从约1到约15个碳原子；烷基或芳基亚砜基团，具有约1到约20个碳原子，最好从约1到约15个碳原子；烷基或芳基亚硫基团，具有约1到约20个碳原子，最好从约1到约15个碳原子；烷基或芳基单或双氨基基团，具有约1到约20个碳原子，最好从约1到约15个碳原子；羟基碳基基团，如上述所定义，携带卤素、羟基、氨基、烷氧基或芳基氧基；当与其所连接的芳香环一起时，形成融合环结构，如萘基；当与R.sub.3一起时，是含有约1到约12个碳原子的烷基基团，最好从约1到约6个碳原子；R.sub.3是氢、甲基、苯基或与之前定义的烷基基团一样的烷基基团；R.sub.4是氢或甲基；当一起时，R.sub.3和R.sub.4是基团.dbd.0；R.sub.5和R.sub.6都是氢，或者一个是氢，另一个是基团，或者一起是基团.dbd.CHN(CH.sub.3).sub.2。
• Pyrido(4,3-b)(1,4) oxazines and pyrido(4,3-b) (1,4)thiazines
  申请人：Southern Research Institute

  公开号：EP0107130A1

  公开（公告）日：1984-05-02

  There are disclosed certain 2H-pyrido[4,3-b]-[1,4]oxazines and 2H-pyrido[4,3-b][1,4]thiazines which posses biological activity. The compounds have the structure: wherein n has a value of 1,2 or 3; X is oxygen or sulfur; R, is a lower alkyl group, e.g., an alkyl group containing up to six carbon atoms such as methyl, ethyl, propyl, butyl, etc.; R2 is a member selected from the group consisting of hydrogen, alkyl radicals having from about one to about 12 carbon atoms, preferably from about one to about six carbon atoms; alkenyl radicals having from about two to about 15 carbon atoms, preferably from about two to about 10 carbon atoms; cycloalkyl radicals having from about three to about 20 carbon atoms, preferably from about three to about 15 carbon atoms: aryl, aralkyl and alkaryl radicals having from about six to about 20 carbon atoms, preferably from about six to about 15 carbon atoms; a halogen radical, e.g., chlorine, fluorine, bromine and iodine; a hydroxyl group; an amino group; a nitro group; an alkoxy or aryloxy group; a carboxyl group or an alkylcarboxyl group having from about one to about 10 carbon atoms, preferably from about one to about five carbon atoms; an alkylthio group or an arylthio group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a sulfonic acid group or alkyl- or arylsulfonyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or arylsulfinyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or aryl mono- or diamino group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a hydrocarbyl group, such as defined above, carrying halogen, hydroxyl, amino, alkoxy or aryloxy; when taken together with the aromatic ring to which it is attached, a fused ring structure such as naphthyl; and, when taken together with R., an alkylene radical containing from about one to about 12 carbon atoms, preferably from about one to about six carbon atoms; R3 is hydrogen, methyl, phenyl or, when taken with R2, an alkylene radical as previously defined; R4 is hydrogen or methyl: R3 and R4, when taken together are the radical = 0; and R5 and R6 are both hydrogen, or one is hydrogen and the other is the radical or where taken together are the radical = CHN(CH3)2-

  已公开的某些 2H-吡啶并[4,3-b]-[1,4]噁嗪和 2H-吡啶并[4,3-b][1,4]噻嗪具有生物活性。这些化合物的结构如下 其中 n 的值为 1、2 或 3；X 为氧或硫；R 为低级烷基，例如R，是低级烷基，例如，含有最多六个碳原子的烷基，如甲基、乙基、丙基、丁基等； R2 是选自下列化合物的成员R2 是选自以下组别的成员：氢、具有约 1 至约 12 个碳原子，最好是约 1 至约 6 个碳原子的烷基；具有约 2 至约 15 个碳原子，最好是约 2 至约 10 个碳原子的烯基；具有约 3 至约 20 个碳原子，最好是约 3 至约 15 个碳原子的环烷基；具有约 6 至约 20 个碳原子，最好是约 6 至约 15 个碳原子的芳基、芳烷基和烷芳基；卤素基，例如：氯、氟、溴、氨、醚、醚、醚、醚、醚、醚、醚、醚、醚、醚、醚、醚、醚、醚、羟基；氨基；硝基；烷氧基或芳氧基；羧基或烷基羧基，具有约 1 至约 10 个碳原子，最好是约 1 至约 5 个碳原子；具有约 1 至约 20 个碳原子，最好是 1 至约 15 个碳原子的烷硫基或芳硫基； 具有约 1 至约 20 个碳原子，最好是 1 至约 15 个碳原子的磺酸基或烷基或芳基磺酰基；具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子的烷基或芳基亚磺酰基； 具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子的烷基或芳基单氨基或二氨基； 如上定义的烃基，带有卤素、羟基、氨基、烷氧基或芳氧基；当与所连接的芳环一起时，为融合环结构，如萘基；当与 R.,R3 是氢、甲基、苯基，或当与 R2 结合时，是如前定义的亚烷基；R4 是氢或甲基：R3 和 R4 合在一起时是基=0；R5 和 R6 都是氢，或一个是氢，另一个是基 或 R5 和 R6 同为基时 = CHN(CH3)2-
• TEMPLE, C. ,, JR;WHEELER, G. P.;COMBER, R. N.;ELLIOTT, R. D.;MONTGOMERY, +, J. MED. CHEM., 1983, 26, N 11, 1614-1619
  作者：TEMPLE, C. ,, JR、WHEELER, G. P.、COMBER, R. N.、ELLIOTT, R. D.、MONTGOMERY, +

  DOI：——

  日期：——
• INHIBITORS OF FTSZ AND USES THEREOF
  申请人：White E. Lucile

  公开号：US20100113429A1

  公开（公告）日：2010-05-06

  The invention relates to inhibitors of FtsZ polymerization and uses thereof.
• US4451650A
  申请人：——

  公开号：US4451650A

  公开（公告）日：1984-05-29