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Cytotoxicity Study of Some Indophenines and Isatin Derivatives

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Cytotoxicity Study of Some Indophenines and Isatin Derivatives A Journal of the Bangladesh Pharmacological Society (BDPS) Bangladesh J Pharmacol 2008; 3: 21-26 Journal homepage: www.banglajol.info Abstracted/indexed in Academic Search Complete, Asia Journals Online, Bangladesh Journals Online, Biological Abstracts, BIOSIS Previews, CAB Abstracts, Current Abstracts, Directory of Open Access Journals, EMBASE/Excerpta Medica, Google Scholar, HINARI (WHO), International Pharmaceutical Abstracts, Open J-gate, Science Citation Index Expanded, SCOPUS and Social Sciences Citation Index; ISSN: 1991-0088 Cytotoxicity study of some indophenines and isatin derivatives Md. Mahbubul Hoque and Md. Rabiul Islam Department of Chemistry, Jahangirnagar University, Savar, Dhaka 1342, Bangladesh. Article Info Abstract Received: 2 December 2007 Eight indophenines were synthesized for the interest of studying biological Accepted: 12 April 2008 activity especially for cytotoxicity. The cytotoxicity of some indophenines and Available Online: 25 April 2008 some isatin derivatives was studied by the brine shrimp lethality bioassay. It DOI: 10.3329/bjp.v3i1.828 was observed that all the indophenines from thiophene, thiazol and isatin Cite this article: derivatives showed potential cytotoxicity against brine shrimp nauplii and Hoque MM, Islam MR. Cytotoxicity the structure activity relationships (SAR) of these compounds have been study of some indophenines and isa- reported. tin derivatives. Bangladesh J Pharma- col. 2008; 3: 21-26. Introduction Materials and Methods Isatin (1H-indole-2,3-dione) and its derivatives possess- Physical and spectral data of the compounds were ing an indole nucleus have arose great attention in recorded on a Fischer Johns electrothermal melting recent years due to their wide variety of biological point apparatus by thin disc method, on a DR-8001 activities and pharmacological studies as insecticides Shimadzu FT-IR spectrophotometer, on a WP-400 NMR (Bahmaria and Deliwala, 1968), fungicides (Chen and spectrophotometer using DMSO-d6 as the solvent with Rhodes, 1996), anti-cancer (Holla et al., 2000) and anti- tetramethylsilane as internal standard and on a Kratas inflammatory. Isatins are very important compounds MS-25 using DH-88 data system. due to their antifungal properties (Islam et al., 1998). Isatin and substituted isatins 1a, 1b and 1c (Sandmeyer, Moreover, isatins are the synthetic precursors of some 1919) were synthesized from the condensation of biologically important compounds such as quinoline 1, corresponding aniline with chloralhydrate and hydro- 2, 3-thiadiazoline (Ram et al., 1980). Besides that, the xylaminehydrochloride followed by the cyclization triazins [5, 6-b] indole-3-thione derivatives have attrac- ted considerable attention in the field of medicine due with concentrated sulfuric acid. Again, some indo- to their antifungal, antimalarial and antiparasitic pro- phenines (Gregory et al., 1993) were synthesized from perties (Pal et al., 1991). Therefore, the research interest thiophene and isatin by the standard procedure. Indo- on isatins has expanded day by day. Because of the phenines 2a and 2b were obtained when isatin reacts continuing interest about isatins and its derivatives with thiophene under refluxing condition in the molar (Saha et al., 1992), the present study aims at the synthe- ratio of 2:1 respectively in the presence of concentrated sis of some indophenines from isatins, thiophene, and sulfuric acid. Indophenines 3a, 3b, 4a and 4b were thiazol. This work has been carried out from the synthe- prepared under identical conditions (as 2a and 2b) from tic point of view along with their biological (Islam et al., 5-chloroisatin and 7-bromoisatin respectively. Again, 1990) property especially cytotoxicity by brine shrimp indophenines 5a and 5b were prepared by the reaction lethality bioassay (Meyer et al., 1982; Solis et al., 1993). between isatin and thiazol in the molar ratio of 2:1 in This work is licensed under a Creative Commons Attribution 4.0 License. You are free to copy, distribute and perform the work. You must attribute the work in the manner specified by the author or licensor. 22 Bangladesh J Pharmacol 2008; 3: 21-26 X a. Chloralhydrate, X O b. Hydroxylaminehydrochloride, c. Conc. Sulfuric acid O NH2 I N Y Y H 1a (X=H, Y=H) 1b (X=Cl, Y=H) 1c (X=H, Y=Br) X X X X S S S + N O O N N O O N Y H H Y Y H H Y 2 a (X=Y=H) 2 b (X=Y=H) a. II S b. Conc. H2SO4 O X X=Cl III IV 3a + 3b 2 O 4a + 4b X=H Y=H Y=Br N a. a. Y S H S b. Conc. H SO b. Conc. H2SO4 2 4 N V a. S b. Tri-ethylamine N N N X X X X S S S + N O O N N O O N Y H H Y Y H H Y 5a X=Y=H 5b X=Y=H Scheme 1 presence of triethylamine under intensive stirring at 80° fresh water and applied for testing. C (Scheme 1). The cytotoxicity of the synthesized Preparation of test sample compounds was studied by brine shrimp lethality bioassay (Solis et al., 1993). For the cytotoxicity study, dimethylsulphoxide (DMSO) was used as a solvent and the mortality of brine shrimp Test animal nauplii in this DMSO solution was almost zero. Differ- Brine shrimps (Artemia Salina) were used as test animal ent concentrations (150, 100 and 50 g/mL) of each test for the investigation of cytotoxicity. samples were prepared with DMSO. Then 10-12 brine shrimp nauplii were transferred to each test tube using Hatching and maintenance of brine shrimp micropipette. The preferred condition for brine shrimp (temperature Counting of nauplii 28-30°C, salinity 30-35 ppt, pH 8-9, and strong aeration) was established by mixing sodium chloride salts in The numbers of survived nauplii in each test tube were water. After obtaining the desired condition, about one counted. The percentage of mortality of brine shrimp teaspoon of brine shrimp eggs was added to the beaker. was calculated for each sample that gives different After 12 hours hatching aggregated brine shrimp mortality for different concentrations. An approximate nauplii were collected in another beaker and rinse with linear correlation was observed when logarithm of Bangladesh J Pharmacol 2008; 3: 21-26 23 concentration was plotted against percentage of 1H-NMR: δ 10.3 (s, 1H, N-H), 7.2-7.4 (m, 6H, aromatic); mortality and the values of LC50 were calculated for M+. each sample. The LC50 represents the concentration of a mass spectrum: m/z 412 ( , 25), 247 (30), 219 (35), compound, which will kill, or inactive 50 percent of the 187 (100), 89 (59) and 77 (60). test animal. LC50 is inversely proportional to the toxicity Reaction IV: The major product 4a was obtained as a of a compound, i.e. the lower the LC50 the higher the blue solid in 55% yield (max 650 nm) after purification toxicity. over silica gel column chromatography. IR: nmax nujul (cm-1) 3312 cm-1 (s, sh, nN-H), 3100 cm-1 (sh, nC-H, -1 -1 Results aromatic), 1716 cm (sh, nC=O), 1653 cm (sh, nC=C); 1H-NMR: δ 11.4 (s, 1H, N-H), 6.9-7.1 (m, 6H, aromatic); Reaction I: After recrystallization, the products 1a, 1b M+. and 1c were obtained as brick-red solids with the yield mass spectrum: m/z 582 ( , 15), 263 (30), 231 of 90% and m. p. ranging from 188°-195°C. The (100), 89 (50) and 77 (70). Second product 4b was structures of the compounds are consistent with the obtained as brown solid, max 620 nm and m. p. 220°- physical constants and spectral data. The IR spectra of 225°C. IR: nmax nujul (cm-1) 3450-3500 cm-1 (m, sh, nN- the compounds 1a-c show a sharp band at 1772 cm-1 H), 3100 cm-1 (sh, nC-H, aromatic), 1716 cm-1 (sh, corresponding to the nC=O keto group and another nC=O), 1693 cm-1 (sh, nC=C); 1H-NMR: δ 9.3 (s, 1H, N- sharp band at 1740 cm-1 indicates the nC=O lactam. H), 8.1-8.2 (d, 2H, alkene), 7.2-7.4 (m, 6H, aromatic); Again, the 1H-NMR signal for >NH is also observed in M+. the respective region as a singlet and a signal for mass spectrum: m/z 500( , 40), 291 (54), 263 (40), aromatic ring as multiplet. 231 (100) and 155 (55). Reaction II: The major product from crude mass Reaction V: The crude was chromatographed on silica afforded 2a in 60% yield, (deep blue, max 625 nm) after gel column to separate the mixture which gives the purification over silica gel column chromatography. IR: major product 5a as a blue solid in 50% yield, m. p. 290° -1 -1 nmax nujul (cm-1) 3450 cm-1 (m, sh, nN-H, lactam), 3100 -295°C. IR: nmax nujul (cm ) 3300 cm (m, sh, nN-H, cm-1 (sh, nC-H, aromatic), 1749 cm-1 (sh, nC=O), 1684 lactam), 3080 cm-1 (sh, nC-H, aromatic), 1716 cm-1 (sh, cm-1 (sh, nC=C) and 1605, 1508 cm-1 (sh, nC=C, nC=O), 1684 cm-1 (sh, nC=N), 1645 (sh, nC=C); 1H- aromatic); 1H-NMR: δ 10.5 (s, 1H, N-H), 7.3-7.5 (m, 4H, NMR: δ 10.0 (s, 1H, N-H, lactam), 8.0 (s, 2H, alkene), 6.9 alkene) and 6.9-7.0 (m, 8H, aromatic); mass spectrum: M+. M+. -7.0 (m, aromatic); mass spectrum: m/z 428 ( , m/z 426 ( , 25), 213 (33), 185 (20), 153 (100), 132 15), 214 (72), 186 (22), 154 (100), 132 (58), 89 (20) and 77 (38), 89 (20) and 77 (66). And 2b was afforded as minor (21).
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