Amino산(酸)으로부터 Anilide유도체(誘導體)의 합성(合成)과 생리활성(生理活性)에 관(關)하여 -제2보(第二報). N-Benzoylglycylanilide 및 N-Benzoylalanylanilide 유도체(誘導體)의 합성(合成)과 생리활성(生理活性)에 관(關)한 연구(硏究)-

Synthesis of Anilide Derivatives from Amino Acids and their Biological Activities -Part II. Synthesis of N-Benzoylglycylanilide and N-Benzoylalanyanilide Derivatives and their Biological Activities-

Glycine, alanine과 aniline 유도체(誘導體)로부터 각각 새로운 N-benzoylglycylanilide 및 N-benzoylalanilide 유도체(誘導體)를 합성(合成)하였다. 이 화합물(化合物)들을 원소분석(元素分析), IR, UV, 그리고 NMR 등(等)의 기기분석(機器分析)에 의(依)하여 N-benzoylglycylanilide, N-benzoyl-glycyl-o-toluidide, N-benzoylglycyl-m-toluidide, N-benzoylglycyl-p-toluidide, N-benzoyl-L-alanylanilide, N-benzoyl-L-alanyl-p-toluidide, N-benzoyl-L-alanyl-m-toluidide, N-benzoyl-L-alanyl-p-toluidide로 각각 동정(同定)되었다. 그리고 합성화합물(合成化合物)들의 벼, 무, 녹두작물(作物)과 잔디종자(種子)에 대한 발아(發芽) 및 생육억제(生育抑制) 효과(效果)를 조사(調査)한 결과(結果)는 다음과 같다. N-benzoyl-L-alanyl-m-toluididie는 무에 대해서 강(强)한 억제효과가 나타남을 볼 수 있었으며, 특히 N-benzoyl-L-alanylanilide는 다른 화합물(化合物)보다 잔디의 생육(生育)을 강(强)하게 억제(抑制)하는 경향(傾向)을 보였다. 대체로 glycine 유도체(誘導體)보다 alanine 유도체(誘導體)가 활성효과(活性效果)가 컸으며, 합성화합물(合成化合物)의 methyl group의 위치(位置)에 따라서 (ortho, meta 그리고 para) 식물종자(種子)의 생육(生育)에 미치는 영향(影響)이 다르게 나타났다. 즉, N-benzoylglycyl-m-toluidide 는 N-benzoylglycyl-o-toluidide와 N-benzolyl-glycyl-p-toluidide보다 식물종자(植物種子) 생육저해활성(生育저沮害活性)이 컸으며, 또한 N-benzoylglycyl-o-toluidide도 역시 N-benzoyl-glycyl-p-toluidide와 N-benzoyl-L-alanyl-m-toluidide보다 크게 나타났다.

N-Benzoylglycylanilide and N-benzoylalanylanilide derivatives were synthesized from N-benzoylglycine and N-benzoylalane with anilines. respectively. The products were identified by elemental analysis, IR, UV and NMR spectra with N-benzoylglycylanilide (I), N-benzoylglycyl-o-toluidide(II), N-benzoylglycyl-m-toluidide(III), N-benzoylglycyl-p-toluidide(IV), N-benzoyl-L-alanylanilide(V), N-bnzoyl-L-alanyl-o-toluidide(VI), N-benzoyl-L-alnnyl-m-toluidise(VII), N-benzoyl-L-alanyl-p-toluidide(VIII). These compounds were tested for their phytotoxicity to the germination and seedling growth of rice, radish, green pea plants and turf grass. Among them, N-benzoyl-Lalanyl-m-toluidide had strongly inhibitory effect on the seedling growth of radish seeds, and N-benzoyl-L-alanylanilide showed an inhibitory activity especially upon the seedling growth of turf seeds. In addition, the inhibitory rate of plant seed growth differed with the isomeric position(ortho, meta and para) of methyl group; N-benzoylglycyl-m-toluidide was more effective than both N-benzoylglycyl-o-toluidide and N-benzoylglycyl-p-toluidide derivatives, and also N-benzoyl-L-alanyl-m-toluidide was more effective than both N-benzoyl-L-alanyl-o-toluidide and N-benzoyl-L-alanyl-p-toluidide.