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4-[3-氯-4-(3-氟苄基氧)苯基氨基]-6-碘喹唑啉 | 231278-20-9

物质功能分类

生物化工 - 提取物 - 植物提取物

分子结构分类

有机化合物 - 有机杂环化合物 - 二氮杂萘

中文名称

4-[3-氯-4-(3-氟苄基氧)苯基氨基]-6-碘喹唑啉

中文别名

4-[3-氯-4-(3-氟苄氧基)苯胺基]-6-碘喹唑啉；4-胺基-N-[3-氯-4-[(3-氟苄基)氧]苯基]-6-碘喹唑啉；N-[3-氯-4-(3-氟苄氧基)苯基]-6-碘-4-喹唑啉胺；N-[3-氯-4-(3-氟苄氧基)苯基]-6-碘喹唑啉-4-胺；4-[3-氯-4-(3-氟苄氧基)苯氨基]-6-碘喹唑啉；拉帕替尼中间体2；N-(3-氯-4-(3-氟苯甲氧基)苯基)-6-碘喹唑啉-4-胺；拉帕替尼中间体 2

英文名称

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

英文别名

6-iodo-4-(3'-chloro-4 '-(3 "-fluorobenzyloxy) phenylamino) quinazoline；N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-iodo-quinazolin-4-amine；N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-iodoquinazolin-4-amine；6-iodo-((4-(3-fluorobenzyloxy)-3-chlorophenyl)-quinazolin-4-yl)amine；6-iodo-(4-(3-fluorobenzyloxy)-3-chlorophenyl)(quinazolin-4-yl)-amine；N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-iodoquinazolin-4-amine；N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine

CAS

231278-20-9

化学式

C₂₁H₁₄ClFIN₃O

mdl

——

分子量

505.718

InChiKey

UHFPFDMMKYQMLC-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

222-224°C
沸点：

581.3±50.0 °C(Predicted)
密度：

1.691±0.06 g/cm3(Predicted)
溶解度：

可溶于DMSO（轻微）、甲醇（轻微、加热）

计算性质

辛醇/水分配系数(LogP)：

6.3
重原子数：

28
可旋转键数：

5
环数：

4.0
sp3杂化的碳原子比例：

0.05
拓扑面积：

47
氢给体数：

1
氢受体数：

5

安全信息

危险品标志：

Xi
海关编码：

2933990090
安全说明：

S26,S36/37/39
危险类别码：

R36/37/38
危险性防范说明：

P261,P305+P351+P338
危险性描述：

H315,H319,H335
储存条件：

-20°C冷冻库

SDS

SDS：bd64f2b8f0dc13742d95c61213fbd8c4

查看

制备方法与用途

用途

拉帕替尼

上下游信息

下游产品

中文名称	英文名称	CAS号	化学式	分子量
拉帕替尼杂质16	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)quinazolin-4-amine	845271-73-0	C₂₁H₁₅ClFN₃O	379.821
——	4-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-quinazolin-6-yl)phenol	1432450-51-5	C₂₇H₁₉ClFN₃O₂	471.918
——	4-{4-[3-chloro-4-(3-fluorobenzyloxy)phenylamino]quinazolin-6-yl}benzaldehyde	1152131-72-0	C₂₈H₁₉ClFN₃O₂	483.929
——	3-(4-(4-(3-fluorobenzyloxy)-3-chlorophenylamino)quinazolin-6-yl)prop-2-ynyl methanesulfonate	1260402-32-1	C₂₅H₁₉ClFN₃O₄S	511.961
——	3-{4-[3-chloro-4-(3-fluorobenzyloxy)phenylamino]quinazolin-6-yl}benzaldehyde	944549-53-5	C₂₈H₁₉ClFN₃O₂	483.929
——	6-(3-(2-(dimethylphosphinoyl)ethylamino)prop-1-ynyl)-N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)quinazolin-4-amine	1260401-99-7	C₂₈H₂₇ClFN₄O₂P	536.973
——	4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(1-oxo-2-butyn-1-yl)quinazoline	908306-45-6	C₂₅H₁₇ClFN₃O₂	445.88
——	(3-{4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)-carbamic acid tert-butyl ester	697299-73-3	C₂₉H₂₆ClFN₄O₃	533.002
——	N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)-6-((E)-3-(4-methyl-1,4-azaphosphino-1-yl)prop-1-enyl)quinazolin-4-amine	1260402-00-3	C₂₉H₂₉ClFN₄O₂P	551.0
——	N-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)-2-morpholinoacetamide	——	C₂₇H₂₅ClFN₅O₃	521.979
——	3-[4-{4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}phenyl]acrylic acid tert-butyl ester	1152131-78-6	C₃₄H₂₉ClFN₃O₃	582.074
——	4-((4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)oxy)butyl N,N-bis(2-chloroethyl)phosphorodiamidate	——	C₂₉H₃₂Cl₃FN₅O₄P	670.935
——	3-((4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)oxy)propyl N,N-bis(2-chloroethyl)phosphorodiamidate	——	C₂₈H₃₀Cl₃FN₅O₄P	656.908
——	3-[3-{4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}phenyl]acrylic acid tert-butyl ester	1257665-57-8	C₃₄H₂₉ClFN₃O₃	582.074
拉帕替尼杂质8	4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(5-hydroxymethylfuran-2-yl)quinazoline	320337-48-2	C₂₆H₁₉ClFN₃O₃	475.907
——	5-{4-[3-chloro-4-(3-fluorobenzyloxy)phenylamino]quinazolin-6-yl}thiophene-2-carbaldehyde	1152131-71-9	C₂₆H₁₇ClFN₃O₂S	489.957
N-去[2-(甲基磺酰基)乙基]拉帕替尼	[6-(5-Aminomethyl-furan-2-yl)-quinazolin-4-yl]-[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-amine	697299-82-4	C₂₆H₂₀ClFN₄O₂	474.922
5-[4-[3-氯-4-(3-氟苯氧基)苯胺基]-6-喹唑啉基]呋喃-2-甲醛	5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde	231278-84-5	C₂₆H₁₇ClFN₃O₃	473.891
——	2-(4-(4-(3-fluorobenzyloxy)-3-chlorophenylamino)quinazolin-6-yl)thiazole-5-carbaldehyde	1227053-00-0	C₂₅H₁₆ClFN₄O₂S	490.945
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-((ethylamino)methyl)-2-furyl)-4-quinazolinamine	1421356-28-6	C₂₈H₂₄ClFN₄O₂	502.976
——	3-[5-{4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}furan-2-yl]acrylic acid	1152131-79-7	C₂₈H₁₉ClFN₃O₄	515.928
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-hydroxyethyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-63-9	C₂₈H₂₄ClFN₄O₃	518.975
拉帕替尼杂质10	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-carboxy-2-furyl)-4-quinazolinamine	1152131-73-1	C₂₆H₁₇ClFN₃O₄	489.89
——	6-(5-((2-(methylthio)ethylamino)methyl)furan-2-yl)-N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)-4-quinazolinamine	1275595-87-3	C₂₉H₂₆ClFN₄O₂S	549.068
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((benzyloxy)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-47-9	C₃₃H₂₆ClFN₄O₃	581.046
——	N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-(5-{[2-(methylsulfonyl)ethoxy]methyl}-furan-2-yl)-4-quinazolinamine	——	C₂₉H₂₅ClFN₃O₅S	582.052
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((4-hydroxybutyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-24-2	C₃₀H₂₈ClFN₄O₃	547.029
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-((n-hexylamino)methyl)-2-furyl)-4-quinazolinamine	1421356-27-5	C₃₂H₃₂ClFN₄O₂	559.083
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((4-methoxybutyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-36-6	C₃₁H₃₀ClFN₄O₃	561.056
——	6-(5-((2-(methylsulfonamido)ethylamino)methyl)furan-2-yl)-N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)quinazolin-4-amine	1275595-88-4	C₂₉H₂₇ClFN₅O₄S	596.082
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((carboxymethyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-50-4	C₂₈H₂₂ClFN₄O₄	532.958
——	6-(5-((2-(methylsulfinyl)ethylamino)methyl)furan-2-yl)-N-(4-(3-fluorobenzyloxy)3-chlorophenyl)-4-quinazolinamine	1275595-86-2	C₂₉H₂₆ClFN₄O₃S	565.068
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((3-chlorobenzyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-38-8	C₃₃H₂₅Cl₂FN₄O₂	599.492
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-((1-(2,3-dihydroxypropyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-68-4	C₂₉H₂₆ClFN₄O₄	549.001
——	6-(5-((2-(sulfamoyl)ethylamino)methyl)furan-2-yl)-N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)quinazolin-4-amine	1275595-85-1	C₂₈H₂₅ClFN₅O₄S	582.055
拉帕替尼	lapatanib	231277-92-2	C₂₉H₂₆ClFN₄O₄S	581.067
——	3-[5-{4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}furan-2-yl]acrylic acid tert-butyl ester	1257665-55-6	C₃₂H₂₇ClFN₃O₄	572.035
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-((5-((cyclohexylmethyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-33-3	C₃₃H₃₂ClFN₄O₂	571.094
——	6-(4-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)-1H-1,2,3-triazol-1-yl)-N-hydroxyhexanamide	——	C₂₉H₂₇ClFN₇O₃	576.03
——	(4-(3-fluoro-benzyloxy)-3-chlorophenyl)-(6-(2-((2-methanesulphonyl-ethylamino)methyl)-thiazol-4-yl)-quinazolin-4-yl)-amine	388082-81-3	C₂₈H₂₅ClFN₅O₃S₂	598.122
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-((bis(2-hydroxyethyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-45-7	C₃₀H₂₈ClFN₄O₄	563.028
——	7-(4-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)-1H-1,2,3-triazol-1-yl)-N-hydroxyheptanamide	——	C₃₀H₂₉ClFN₇O₃	590.057
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-carboxypropyl)amino)methyl)-2-furyl)-4-quinazolinamine	——	C₃₀H₂₆ClFN₄O₄	561.012
——	(S)-N-(4-(3-fluorobenzyl-oxy)-3-chlorophenyl)-6-(5-(1-(amino)-2-(methylthio)ethyl)furan-2-yl)quinazolin-4-amine	1235820-61-7	C₂₈H₂₄ClFN₄O₂S	535.042
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-(4-hydroxyphenyl)ethyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-40-2	C₃₄H₂₈ClFN₄O₃	595.073
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-ethoxycarbonylethyl)amino)methyl)-2-furyl)-4-quinazolinamine	1012058-22-8	C₃₁H₂₈ClFN₄O₄	575.039
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-((((4-carboxy-4-amino)butyl)amino)methyl)-2-furyl)-4-quinazolinamine	——	C₃₁H₂₉ClFN₅O₄	590.054
——	N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(5-(piperazin-1-ylmethyl)furan-2-yl)quinazolin-4-amine	——	C₃₀H₂₇ClFN₅O₂	544.028
——	N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(5-((2-(methylsulfonyl)ethylimino)methyl)furan-2-yl)quinazolin-4-amine	1227853-06-6	C₂₉H₂₄ClFN₄O₄S	579.051
——	NEU-0000387	——	C₃₁H₃₀ClFN₄O₄S	609.121
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2,6-dihydroxyhexyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-44-6	C₃₂H₃₂ClFN₄O₄	591.082
——	NEU-0000379	——	C₃₁H₃₀ClFN₄O₄S	609.121
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((3-aminocyclohexyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-49-1	C₃₂H₃₁ClFN₅O₂	572.082
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-((((3-chlorocyclohexyl)methyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-35-5	C₃₃H₃₁Cl₂FN₄O₂	605.539
——	6-(5-((2-(2,2,2-trifluoroethylsulfonyl)ethylamino)methyl)furan-2-yl)-N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)quinazolin-4-amine	1275595-89-5	C₃₀H₂₅ClF₄N₄O₄S	649.066
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-(3-chloro-5-fluorophenyl)ethyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-43-5	C₃₄H₂₆Cl₂F₂N₄O₂	631.509
——	(S)-N-(4-(3-fluorobenzyl-oxy)-3-chlorophenyl)-6-(5-(1-(amino)-2-(methylsulfinyl)ethyl)furan-2-yl)quinazolin-4-amine	1235822-15-7	C₂₈H₂₄ClFN₄O₃S	551.041
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-(3-hydroxy-5-fluorophenyl)ethyl)amino)methyl)-2-furyl)-4-quinazolinamine	1421356-42-4	C₃₄H₂₇ClF₂N₄O₃	613.063
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-(4-nitrophenyl)ethyl)amino)methyl )-2-furyl)-4-quinazolinamine	1421356-39-9	C₃₄H₂₇ClFN₅O₄	624.071
——	(S)-6-(5-(1-amino-2-(methylsulfonyl)ethyl)furan-2-yl)-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)quinazolin-4-amine	1235822-68-0	C₂₈H₂₄ClFN₄O₄S	567.04
——	(R)-6-(5-(1-amino-2-(methylsulfonyl)ethyl)furan-2-yl)-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)quinazolin-4-amine	1235822-94-2	C₂₈H₂₄ClFN₄O₄S	567.04
——	NEU-0000380	——	C₃₄H₂₇ClFN₃O₅S	644.123
——	(E)-N-(2-aminophenyl)-3-(5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-yl)acrylamide	1152131-91-3	C₃₄H₂₅ClFN₅O₃	606.056
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-((((1-carboxy-3-methylthio)propyl)amino)methyl)-2-furyl)-4-quinazolinamine	——	C₃₁H₂₈ClFN₄O₄S	607.105
——	N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-(5-{[[2-(methylsulfonyl)ethyl](propyl)-amino]methyl}-furan-2-yl)-4-quinazolinamine	——	C₃₂H₃₂ClFN₄O₄S	623.148
——	(S)-N-(4-(3-fluorobenzyl-oxy)-3-chlorophenyl)-6-(5-(1-(methylamino)-2-(methylthio)ethyl)furan-2-yl)quinazolin-4-amine	1235820-63-9	C₂₉H₂₆ClFN₄O₂S	549.068
——	2-{{[5-(4-{3-chloro-4-[(3-fluorobenzyl)oxy]anilino}-6-quinazolinyl)-furan-2-yl]methyl}[2-(methylsulfonyl)ethyl]amino}acetonitrile	——	C₃₁H₂₇ClFN₅O₄S	620.104
——	NEU-0000388	——	C₃₆H₃₂ClFN₄O₄S	671.192
——	(4-(3-fluorobenzyloxy)-3-chlorophenyl)-(6-(2-((2-phenylsulphonyl-ethylamino)-methyl)-furan-2-yl)-quinazolin-4-yl)-amine	——	C₃₄H₂₈ClFN₄O₄S	643.138
——	3-[5-{4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}furan-2-yl]-N-(tetrahydropyran-2-yloxy)acrylamide	1152131-83-3	C₃₃H₂₈ClFN₄O₅	615.061
——	ethyl 4-((5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-yl)methyl)piperazine-1-carboxylate	——	C₃₃H₃₁ClFN₅O₄	616.092
——	5-{4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-furan-2-carboxylic acid methoxy-methyl-amide	1009307-38-3	C₂₈H₂₂ClFN₄O₄	532.958
——	5-{4-[3-chloro-4-(3-fluorobenzyloxy)phenylamino]quinazolin-6-yl}thiophene-2-carboxylic acid (2-aminophenyl)amide	1152131-90-2	C₃₂H₂₃ClFN₅O₂S	596.084
——	(4-(3-fluorobenzyloxy)-3-chlorophenyl)-(6-(2-((2-(pyridin-2-yl)-sulphonyl-ethylamino)-methyl)-furan-2-yl)-quinazolin-4-yl)-amine	——	C₃₃H₂₇ClFN₅O₄S	644.126
——	5-{4-[3-chloro-4-(3-fluorobenzyloxy)phenylamino]quinazolin-6-yl}furan-2-carboxylic acid (2-aminophenyl)amide	1152131-89-9	C₃₂H₂₃ClFN₅O₃	580.018
——	(4-(3-fluorobenzyloxy)-3-chlorophenyl)-(6-(2-((2-(2-N-methylimidazolyl)-sulphonyl-ethylamino)-methyl)-furan-2-yl)-quinazolin-4-yl)-amine	——	C₃₂H₂₈ClFN₆O₄S	647.13
——	5-{4-[3-chloro-4-(3-fluorobenzyloxy)phenylamino]quinazolin-6-yl}thiophene-2-carboxylic acid (tetrahydropyran-2-yloxy)amide	1152131-88-8	C₃₁H₂₆ClFN₄O₄S	605.089
——	N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(1-(dimethylamino)-2-(methylsulfonyl)ethyl)furan-2-yl)quinazolin-4-amine	1227051-80-0	C₃₀H₂₈ClFN₄O₄S	595.094
——	5-{4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}furan-2-carboxylic acid (tetrahydropyran-2-yloxy)amide	1152131-87-7	C₃₁H₂₆ClFN₄O₅	589.023

反应信息

作为反应物：

描述：

4-[3-氯-4-(3-氟苄基氧)苯基氨基]-6-碘喹唑啉在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 sodium triacetoxyborohydride 、三乙胺作用下，以乙醇为溶剂，反应 4.5h，生成 6-(5-((2-(methylsulfinyl)ethylamino)methyl)furan-2-yl)-N-(4-(3-fluorobenzyloxy)3-chlorophenyl)-4-quinazolinamine

参考文献：

名称：

Discovery of a potent dual EGFR/HER-2 inhibitor L-2 (selatinib) for the treatment of cancer

摘要：

To develop potent dual EGFR/HER-2 inhibitors with improved druggability, a series of new lapatinib analogs were designed and synthesized. Compared with lapatinib, L-2, L-4 and M-6 were more active against BT-474 or NCI-N87 cells. In vivo efficacy studies indicated that L-2 significantly suppressed tumor growth in NCI-N87 (94.8% inhibition) or SK-OV-3 xenograft (85.7% inhibition) without causing significant loss of body weight. And the inhibition rates of lapatinib in the two xenograft models were 89.7% and 78.8%, respectively. Moreover, further studies revealed that the potent in vivo activities of L-2 may be mainly attributed to its superior aqueous solubility and oral bioavailability. In addition, a high-yielding one-pot procedure was developed for the synthesis of lapatinib and its analogs. (C) 2013 Elsevier Masson SAS. All tights reserved.

DOI：

10.1016/j.ejmech.2013.09.032
作为产物：

描述：

6-碘-4(H)-喹唑啉酮在氯化亚砜、 N,N-二甲基甲酰胺作用下，以异丙醇为溶剂，反应 2.0h，生成 4-[3-氯-4-(3-氟苄基氧)苯基氨基]-6-碘喹唑啉

参考文献：

名称：

具有异羟肟酸部分的新型6-（1,2,3-三唑-4-基）-4-氨基喹唑啉衍生物的合成和研究，用于癌症治疗。

摘要：

通过将EGFR / HER2和HDAC抑制剂的关键药效团合并为一个化合物，合成了一系列新的EGFR，HER-2和HDAC多靶点抑制剂。化合物9a-1含有4-苯胺基喹唑啉和C-6三唑连接的异羟肟酸长烷基链，对这些酶表现出优异的抑制作用（化合物9d对野生型EGFR，HDAC1和HDAC6表现出最佳的抑制效能，IC50值分别为0.12 nM，0.72nM和3.2nM）。此外，化合物9b和9d有效抑制了五种人类癌细胞系的增殖（IC50值在0.49至8.76μM之间）。进一步的机理研究表明，化合物9d在细胞水平上还调节EGFR和HER2的磷酸化以及组蛋白H3的超乙酰化，并诱导BT-474细胞显着的凋亡。所以，

DOI：

10.1016/j.bmc.2016.10.006

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文献信息

PROTOZOAN PARASITE GROWTH INHIBITORS

申请人：Northeastern University

公开号：US20150259331A1

公开（公告）日：2015-09-17

Compounds and methods for inhibiting growth of a protozoan parasite. Methods of treating a protozoan parasite infection in a subject by administering a therapeutically effective amount of a compound as disclosed herein. The compounds and methods can be used to inhibit growth of protozoan parasites such as Trypanosoma brucei, Trypanosoma cruzi, Leishmania spp., and Plasmodium spp.

用于抑制原生动物寄生虫生长的化合物和方法。通过向主体施用如本文所述的治疗有效量的化合物来治疗原生动物寄生虫感染的方法。这些化合物和方法可用于抑制如非洲锥虫、克鲁兹锥虫、利什曼原虫属和疟原虫属等原生动物寄生虫的生长。
Synthesis and in vitro biological evaluation of novel quinazoline derivatives

作者：Yaling Zhang、Ying Zhang、Juan Liu、Li Chen、Lijun Zhao、Baolin Li、Wei Wang

DOI：10.1016/j.bmcl.2017.02.027

日期：2017.4

A series of novel 4-arylamino-6-(5-substituted furan-2-yl)quinazoline derivatives were designed, synthesized and evaluated on biological activities in vitro. Compound 2a, 3a and 3c exhibited highly anti-proliferation activities on all tested tumor cell lines including SW480, A549, A431 and NCI-H1975 cells. Especially, compound 2a not only exhibited strong anti-proliferation activities against the tumor

设计，合成了一系列新型的4-芳基氨基-6-（5-取代的呋喃-2-基）喹唑啉衍生物，并对其体外生物活性进行了评价。化合物2a，3a和3c在所有测试的肿瘤细胞系（包括SW480，A549，A431和NCI-H1975细胞）上均表现出高度的抗增殖活性。特别地，化合物2a不仅对表达野生型或突变型EGFRL858R / T790M的肿瘤细胞系表现出强的抗增殖活性，而且还显示出对野生型EGFR的最有效的抑制活性（IC 50 ＝ 5.06nM）。与EGFR对接的结果表明2a的结合模式与拉帕替尼相似。Western印迹分析显示2a在指定浓度下能明显抑制肺癌细胞中EGFR，Akt和Erk1 / 2的活化。
[EN] A NOVEL PROCESS FOR THE PREPARATION OF LAPATINIB AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS<br/>[FR] NOUVEAU PROCÉDÉ DE PRÉPARATION DE LAPATINIB ET DE SES SELS DE QUALITÉ PHARMACEUTIQUE

申请人：NATCO PHARMA LTD

公开号：WO2010061400A1

公开（公告）日：2010-06-03

The present invention relates to an improved and novel process for the preparation of high purity crystalline base of Lapatinib of formula-(l) having chemical name N-3-chloro-4-[(3- fluorobenzyloxy]phenyl}-6-[5-([2-(methanesuIfonyl) ethyl]amino}methyl]-2-furyl]-4-quin - azolinamine and its pharmaceutically acceptable salts. The present invention further relates to intermediates according to formula (8) and formula (9) used in this process

本发明涉及一种改进的和新颖的制备高纯度拉帕替尼晶态碱的工艺，其化学名为N-3-氯-4-[(3-氟苯甲基氧基]苯基}-6-[5-([2-(甲磺酰基)乙基]氨基}甲基]-2-呋喃基]-4-喹唑啉胺，及其药用可接受的盐。本发明进一步涉及在此工艺中使用的根据公式(8)和公式(9)的中间体。
N’-芳基-N，N-二甲基甲脒的制备新方法

申请人：陕西师范大学

公开号：CN103539702B

公开（公告）日：2016-03-30

本发明提供了一种合成N’-芳基-N，N-二甲基甲脒的新方法。该方法先以N，N-二甲基甲酰胺与硫酸二甲酯反应成亚胺盐；生成的亚胺盐在碱的存在下，与芳胺反应生成N’-芳基-N，N-二甲基甲脒；该甲脒可与其它胺作用生成喹唑啉类化合物，可用于抗肿瘤药物埃罗替尼、拉帕替尼和吉非替尼等的合成。该方法反应条件温和，适合于工业化生产。
Oxalic Diamides and <i>tert</i>-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction

作者：Zhixiang Chen、Yongwen Jiang、Li Zhang、Yinlong Guo、Dawei Ma

DOI：10.1021/jacs.8b12142

日期：2019.2.27

A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic

已经开发了一种用于制备烷基芳基醚的稳健实用的方案，该方案依赖于使用两种类型的配体来促进 Cu 催化的（杂）芳基卤化物的烷氧基化。反应范围非常适用于各种偶联伙伴，尤其是具有挑战性的仲醇和（杂）芳基氯。在与芳基氯化物和溴化物偶联的情况下，两个草酸二酰胺作为强大的配体。叔丁醇首先被证明是铜催化偶联反应的配体，导致芳基碘化物在室温下完成烷氧基化。此外，许多碳水化合物衍生物适用于该偶联反应，以 29-98% 的产率提供相应的碳水化合物-芳基醚。