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首页> 外文期刊>Acta crystallographica. Section C, Structural chemistry. >Synthesis, crystal structures and anti‐inflammatory activity of fluorine‐substituted 1,4,5,6‐tetrahydrobenzo[ h h ]quinazolin‐2‐amine derivatives
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Synthesis, crystal structures and anti‐inflammatory activity of fluorine‐substituted 1,4,5,6‐tetrahydrobenzo[ h h ]quinazolin‐2‐amine derivatives

机译：氟取代的1,4,5,6-四氢苯并[H H]喹唑啉-2-胺衍生物的合成，晶体结构和抗炎活性

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Two fluorine‐substituted 1,4,5,6‐tetrahydrobenzo[ h ]quinazolin‐2‐amine (BQA) derivatives, namely 2‐amino‐4‐(2‐fluorophenyl)‐9‐methoxy‐1,4,5,6‐tetrahydrobenzo[ h ]quinazolin‐3‐ium chloride, ( 8 ), and 2‐amino‐4‐(4‐fluorophenyl)‐9‐methoxy‐1,4,5,6‐tetrahydrobenzo[ h ]quinazolin‐3‐ium chloride, ( 9 ), both C 19 H 19 FN 3 O + ·Cl ? , were generated by Michael addition reactions between guanidine hydrochloride and the α,β‐unsaturated ketones ( E )‐2‐(2‐fluorobenzylidene)‐7‐methoxy‐3,4‐dihydronaphthalen‐1(2 H )‐one, C 18 H 15 FO 2 , ( 6 ), and ( E )‐2‐(4‐fluorobenzylidene)‐7‐methoxy‐3,4‐dihydronaphthalen‐1(2 H )‐one, ( 7 ). Because both sides of α,β‐unsaturated ketones ( 6 ) or ( 7 ) can be attacked by guanidine, we obtained a pair of isomers in ( 8 ) and ( 9 ). Single‐crystal X‐ray diffraction indicates that each isomer has a chiral C atom and both ( 8 ) and ( 9 ) crystallize in the achiral space group P 2 1 / c . The chloride ion, as a hydrogen‐bond acceptor, plays an important role in the formation of multiple hydrogen bonds. Thus, adjacent molecules are connected through intermolecular hydrogen bonds to generate a banded structure. Furthermore, these bands are linked into an interesting 3D network via hydrogen bonds and π–π interactions. Fortunately, the solubilities of ( 8 ) and ( 9 ) were distinctly improved and can exceed 50?mg?ml ?1 in water or PBS buffer system (pH 7.4) at room temperature. In addition, the results of an investigation of anti‐inflammatory activity show that ( 8 ) and ( 9 ), with o ‐ and p ‐fluoro substituents, respectively, display more potential for inhibitory effects on LPS‐induced NO secretion than starting ketones ( 6 ) and ( 7 ).
机译：两个氟取代的1,4,5,6-四氢苯并[H]喹唑啉-2-胺（BQA）衍生物，即2-氨基-4-（2-氟苯基）-9-甲氧基-1,4,5,6 -tetrahydrobenzo [h]喹唑啉-3-氯化物，（8）和2-氨基-4-（4-氟苯基）-9-甲氧基-1,4,5,6-四氢苯-3-Ium氯化物，（9），C 19 H 19 FN 3 O +·CL？ ，由盐酸胍和α，β-不饱和酮（E）-2-（2-氟苄基）-7-甲氧基-3,4-二氢萘-1（2小时） - ONE，C 18之间的Michael添加反应产生H 15 Fo 2，（6）和（E）-2-（4-氟苄基）-7-甲氧基-3,4-二氢萘-1（2小时） - （7）。因为α，β-不饱和酮（6）或（7）的两侧可以被胍攻击，我们在（8）和（9）中获得了一对异构体。单晶X射线衍射表明，每个异构体具有手性C原子，并且（8）和（9）均在成立空间组P 2 1 / C中结晶。作为氢粘合受体的氯离子在形成多个氢键的形成中起重要作用。因此，相邻分子通过分子间氢键连接以产生带状结构。此外，这些带通过氢键和π-π相互作用链接成有趣的3D网络。幸运的是，（8）和（9）的溶解度明显改善，在室温下水或PBS缓冲体系（pH7.4）中的50？mg？1。此外，抗炎活性研究结果表明（8）和（9）分别与O - 和P-氟代取代物分别显示出更多抑制对LPS诱导的抑制作用的可能性而不是起始酮（ 6）和（7）。

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