Dubey S K, Singh A K, Singh H, Sharma S, Iyer R N, Katiyar J C, Goel P, Sen A B
J Med Chem. 1978 Nov;21(11):1178-81. doi: 10.1021/jm00209a020.
A series of substituted 1-hydroxy-2-naphthanilides 4--14 has been synthesized by treating 1-hydroxy-2-naphthoic acids 2 with substituted anilines 3. The nitronaphthanilides, on reduction and subsequent treatment with thiophosgene, gave the corresponding substituted 2-naphthanilide isothiocyanates 30--33. Substitution of the chlorine of 8 by various cyclic amines gave 3'-nitro-4'-substituted 1-hydroxy-2-naphthanilides 15--21. Various 3-aryl-4-oxo-2,3-dihydro-1,3-naphthoxazine-2-thiones 34-43 and 3 aryl-2,4-dioxo-2,3-dihydro-1,3-naphthoxazines 44--51 have been prepared by reacting the corresonding naphthanilides with thiophosgene and ethyl chloroformate, respectively. All the compounds were tested for their cestodicidal activity against Hymenolepis nana infection in rats; 30 was found to be the most active compound of the series, showing 100% clearance of infection at a single oral dose of 7.5 mg/kg.
通过用取代苯胺3处理1-羟基-2-萘甲酸2，合成了一系列取代的1-羟基-2-萘甲酰苯胺4 - 14。硝代萘甲酰苯胺经还原并随后用硫光气处理，得到相应的取代的2-萘甲酰苯胺异硫氰酸酯30 - 33。用各种环状胺取代8位的氯，得到3'-硝基-4'-取代的1-羟基-2-萘甲酰苯胺15 - 21。通过使相应的萘甲酰苯胺分别与硫光气和氯甲酸乙酯反应，制备了各种3-芳基-4-氧代-2,3-二氢-1,3-萘并恶嗪-2-硫酮34 - 43和3-芳基-2,4-二氧代-2,3-二氢-1,3-萘并恶嗪44 - 51。测试了所有化合物对大鼠微小膜壳绦虫感染的杀绦虫活性；发现30是该系列中活性最高的化合物，在口服单剂量7.5 mg/kg时显示出100%的感染清除率。
