Evaluation of anticancer activity of 4-vinyl-1-arylsulfonylimidazolidinones
To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with broad spectrum, three 1-(arylsulfonyl)-4-vinylimidazolidinones (2) were synthesized from methyl serinate (3) in 8 steps. Reaction of intermediate...
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| Published in | Archives of pharmacal research Vol. 29; no. 9; pp. 721 - 727 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Korea (South)
대한약학회
01.09.2006
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| Subjects | |
| Online Access | Get full text |
| ISSN | 0253-6269 1976-3786 |
| DOI | 10.1007/BF02974070 |
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| Abstract | To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with broad spectrum, three 1-(arylsulfonyl)-4-vinylimidazolidinones (2) were synthesized from methyl serinate (3) in 8 steps. Reaction of intermediate 2-phenoxycarbonylaminobut-3-enyl p-toluenesulfonate (10) with arylsulfonamide in the presence of potassium carbonate produced corresponding 2 and N-(4-vinyloxazolidin-2-yl)arylsulfonamide 11 in approximately equal ratio. This reaction is believed to undergo through urea intermediate 16 as shown in scheme 3. 1-Arylsufonyl-4-vinylimidazolidinones 2 show much reduced activity against human colon carcinoma (Colo205), human chronic myelogenous leukemia (K562), and human ovarian adenocarcinoma (SK-OV-3) and compatible activity against human lung carcinoma (A549) compared to 1. Therefore phenyl at 4-position should be the optimum planar motif for the activity of 1. |
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| AbstractList | To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with broad spectrum, three 1-(arylsulfonyl)-4-vinylimidazolidinones (2) were synthesized from methyl serinate (3) in 8 steps. Reaction of intermediate 2-phenoxycarbonylaminobut-3-enyl p-toluenesulfonate (10) with arylsulfonamide in the presence of potassium carbonate produced corresponding 2 and N-(4-vinyloxazolidin-2-yl)arylsulfonamide 11 in approximately equal ratio. This reaction is believed to undergo through urea intermediate 16 as shown in scheme 3. 1-Arylsufonyl-4-vinylimidazolidinones 2 show much reduced activity against human colon carcinoma (Colo205), human chronic myelogenous leukemia (K562), and human ovarian adenocarcinoma (SK-OV-3) and compatible activity against human lung carcinoma (A549) compared to 1. Therefore phenyl at 4-position should be the optimum planar motif for the activity of 1.To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with broad spectrum, three 1-(arylsulfonyl)-4-vinylimidazolidinones (2) were synthesized from methyl serinate (3) in 8 steps. Reaction of intermediate 2-phenoxycarbonylaminobut-3-enyl p-toluenesulfonate (10) with arylsulfonamide in the presence of potassium carbonate produced corresponding 2 and N-(4-vinyloxazolidin-2-yl)arylsulfonamide 11 in approximately equal ratio. This reaction is believed to undergo through urea intermediate 16 as shown in scheme 3. 1-Arylsufonyl-4-vinylimidazolidinones 2 show much reduced activity against human colon carcinoma (Colo205), human chronic myelogenous leukemia (K562), and human ovarian adenocarcinoma (SK-OV-3) and compatible activity against human lung carcinoma (A549) compared to 1. Therefore phenyl at 4-position should be the optimum planar motif for the activity of 1. To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with broad spectrum, three 1-(arylsulfonyl)- 4-vinylimidazolidinones (2) were synthesized from methyl serinate (3) in 8 steps. Reaction of intermediate 2-phenoxycarbonylaminobut-3-enyl p-toluenesulfonate (10) with arylsulfonamide in the presence of potassium carbonate produced corresponding 2 and N-(4-vinyloxazolidin- 2-yl)arylsulfonamide 11 in approximately equal ratio. This reaction is believed to undergo through urea intermediate 16 as shown in scheme 3. 1-Arylsufonyl-4-vinylimidazolidinones 2 show much reduced activity against human colon carcinoma (Colo205), human chronic myelogenous leukemia (K562), and human ovarian adenocarcinoma (SK-OV-3) and compatible activity against human lung carcinoma (A549) compared to 1. Therefore phenyl at 4-position should be the optimum planar motif for the activity of 1 KCI Citation Count: 9 To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with broad spectrum, three 1-(arylsulfonyl)-4-vinylimidazolidinones (2) were synthesized from methyl serinate (3) in 8 steps. Reaction of intermediate 2-phenoxycarbonylaminobut-3-enyl p-toluenesulfonate (10) with arylsulfonamide in the presence of potassium carbonate produced corresponding 2 and N-(4-vinyloxazolidin-2-yl)arylsulfonamide 11 in approximately equal ratio. This reaction is believed to undergo through urea intermediate 16 as shown in scheme 3. 1-Arylsufonyl-4-vinylimidazolidinones 2 show much reduced activity against human colon carcinoma (Colo205), human chronic myelogenous leukemia (K562), and human ovarian adenocarcinoma (SK-OV-3) and compatible activity against human lung carcinoma (A549) compared to 1. Therefore phenyl at 4-position should be the optimum planar motif for the activity of 1. |
| Author | Hoang, Le Tuan Anh Shin, Hye-Rim Jung, Sang-Hun Bang, Seong-Cheol Lee, Ki-Cheul Kwak, Son-Hyok Seo, Hyun-Hee |
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| CitedBy_id | crossref_primary_10_1002_anie_201806295 crossref_primary_10_1039_c0md00219d crossref_primary_10_1016_j_tet_2011_07_087 crossref_primary_10_1002_ange_201806295 crossref_primary_10_1002_ardp_200700178 crossref_primary_10_1134_S1070363219090329 crossref_primary_10_1021_acscatal_4c05973 crossref_primary_10_5012_bkcs_2014_35_10_2922 crossref_primary_10_1007_s12272_018_1003_9 crossref_primary_10_3109_14756366_2015_1022172 crossref_primary_10_1021_acscatal_1c02721 |
| Cites_doi | 10.1007/BF02976463 10.1007/BF02975152 10.1016/j.bmcl.2004.09.069 10.1016/S0006-2952(02)01105-X 10.1007/BF03179923 10.1016/0040-4020(96)00672-2 10.1016/0960-894X(96)00463-5 10.1021/jo00388a004 10.1016/S0304-3835(99)00070-1 10.1016/S0968-0896(03)00530-3 10.1007/BF02986031 10.1246/cl.1987.2085 10.1007/BF02976159 10.1007/BF02980119 10.1007/BF02975244 |
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| References | S. Kim (BF02974070_CR11) 2004; 14 S.-H. Jung (BF02974070_CR4) 1996; 6 C. H. Lee (BF02974070_CR13) 2002; 64 S. H. Jung (BF02974070_CR7) 2000; 23 D. A. Scudiero (BF02974070_CR17) 1988; 48 H.-Y. Choo Park (BF02974070_CR1) 2003; 11 S.-H. Jung (BF02974070_CR5) 1997; 20 D. D. Perrin (BF02974070_CR16) 1982 E.-Y. Moon (BF02974070_CR15) 1999; 140 L. Williams (BF02974070_CR18) 1996; 36 S.-H. Jung (BF02974070_CR8) 2001; 24 S.-H. Jung (BF02974070_CR3) 1996; 19 BF02974070_CR19 BF02974070_CR9 P. Ganer (BF02974070_CR2) 1987; 52 S.-H. Jung (BF02974070_CR6) 1998; 8 H.-S. Lee (BF02974070_CR12) 2000; 23 BF02974070_CR14 I.-W. Kim (BF02974070_CR10) 2003; 26 |
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| Snippet | To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with... To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with... |
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| SubjectTerms | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Drug Screening Assays, Antitumor Humans Hydantoins - chemical synthesis Hydantoins - pharmacology Spectrophotometry, Ultraviolet Structure-Activity Relationship Tetrazolium Salts Thiazoles Vinyl Compounds - chemical synthesis Vinyl Compounds - pharmacology 약학 |
| Title | Evaluation of anticancer activity of 4-vinyl-1-arylsulfonylimidazolidinones |
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