Synthesis, Anticancer Activity, and Molecular Modeling of New Halogenated Spiro[pyrrolidine-thiazolo-oxindoles] Derivatives
A one-pot, single-step, and an atom-economical process towards the synthesis of highly functionalized spirooxindoles analogues was efficiently conducted to produce a satisfactory chemical yields (70−93%) with excellent relative diastereo-, and regio-selectivity. An in vitro antiproliferati...
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MDPI AG
2020-03-01
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| Series: | Applied Sciences |
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| Online Access: | https://www.mdpi.com/2076-3417/10/6/2170 |
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| author | Mohammad Shahidul Islam Abdullah Mohammed Al-Majid Fardous F. El-Senduny Farid A. Badria A. F. M. Motiur Rahman Assem Barakat Yaseen A. M. M. Elshaier |
| author_facet | Mohammad Shahidul Islam Abdullah Mohammed Al-Majid Fardous F. El-Senduny Farid A. Badria A. F. M. Motiur Rahman Assem Barakat Yaseen A. M. M. Elshaier |
| author_sort | Mohammad Shahidul Islam |
| collection | DOAJ |
| description | A one-pot, single-step, and an atom-economical process towards the synthesis of highly functionalized spirooxindoles analogues was efficiently conducted to produce a satisfactory chemical yields (70−93%) with excellent relative diastereo-, and regio-selectivity. An in vitro antiproliferative assay was carried out on different cancer cell lines to evaluate the biological activity of the synthesized tetrahydro-1’<i>H</i>-spiro[indoline-3,5’-pyrrolo[1,2-<i>c</i>]thiazol]-2-one <b>5a−n.</b> The prepared hybrids were then tested <i>in vitro</i> for their antiproliferative effects against three cancer cell lines, namely, HepG2 (liver cancer), MCF-7 (breast cancer), and HCT-116 (colon cancer). The spirooxindole analogue <b>5g</b> exhibited a broad activity against HepG2, MCF-7, and HCT-116 cell lines of liver, breast, and colorectal cancers when compared to <i>cis</i>platin. Modeling studies including shape similarity, lipophilicity scores, and physicochemical parameters were calculated. The results of this study indicated that spirooxindole analogue <b>5g</b> retained a good physiochemical parameters with acceptable lipophilicity scores. |
| first_indexed | 2024-12-18T15:03:38Z |
| format | Article |
| id | doaj.art-accc51d835e142bf943129e58a6a2b58 |
| institution | Directory Open Access Journal |
| issn | 2076-3417 |
| language | English |
| last_indexed | 2024-12-18T15:03:38Z |
| publishDate | 2020-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Applied Sciences |
| spelling | doaj.art-accc51d835e142bf943129e58a6a2b582022-12-21T21:03:51ZengMDPI AGApplied Sciences2076-34172020-03-01106217010.3390/app10062170app10062170Synthesis, Anticancer Activity, and Molecular Modeling of New Halogenated Spiro[pyrrolidine-thiazolo-oxindoles] DerivativesMohammad Shahidul Islam0Abdullah Mohammed Al-Majid1Fardous F. El-Senduny2Farid A. Badria3A. F. M. Motiur Rahman4Assem Barakat5Yaseen A. M. M. Elshaier6Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Mansura University, Mansura 35516, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, EgyptDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Organic and Medicinal chemistry, Faculty of Pharmacy, University of Sadat City, Sadat City, Menoufiya 32958, EgyptA one-pot, single-step, and an atom-economical process towards the synthesis of highly functionalized spirooxindoles analogues was efficiently conducted to produce a satisfactory chemical yields (70−93%) with excellent relative diastereo-, and regio-selectivity. An in vitro antiproliferative assay was carried out on different cancer cell lines to evaluate the biological activity of the synthesized tetrahydro-1’<i>H</i>-spiro[indoline-3,5’-pyrrolo[1,2-<i>c</i>]thiazol]-2-one <b>5a−n.</b> The prepared hybrids were then tested <i>in vitro</i> for their antiproliferative effects against three cancer cell lines, namely, HepG2 (liver cancer), MCF-7 (breast cancer), and HCT-116 (colon cancer). The spirooxindole analogue <b>5g</b> exhibited a broad activity against HepG2, MCF-7, and HCT-116 cell lines of liver, breast, and colorectal cancers when compared to <i>cis</i>platin. Modeling studies including shape similarity, lipophilicity scores, and physicochemical parameters were calculated. The results of this study indicated that spirooxindole analogue <b>5g</b> retained a good physiochemical parameters with acceptable lipophilicity scores.https://www.mdpi.com/2076-3417/10/6/2170spirooxindole1,3-dipolar cycloadditioneco-friendly chemistryrocsshape alignmentlipophilicityanticancer activity |
| spellingShingle | Mohammad Shahidul Islam Abdullah Mohammed Al-Majid Fardous F. El-Senduny Farid A. Badria A. F. M. Motiur Rahman Assem Barakat Yaseen A. M. M. Elshaier Synthesis, Anticancer Activity, and Molecular Modeling of New Halogenated Spiro[pyrrolidine-thiazolo-oxindoles] Derivatives Applied Sciences spirooxindole 1,3-dipolar cycloaddition eco-friendly chemistry rocs shape alignment lipophilicity anticancer activity |
| title | Synthesis, Anticancer Activity, and Molecular Modeling of New Halogenated Spiro[pyrrolidine-thiazolo-oxindoles] Derivatives |
| title_full | Synthesis, Anticancer Activity, and Molecular Modeling of New Halogenated Spiro[pyrrolidine-thiazolo-oxindoles] Derivatives |
| title_fullStr | Synthesis, Anticancer Activity, and Molecular Modeling of New Halogenated Spiro[pyrrolidine-thiazolo-oxindoles] Derivatives |
| title_full_unstemmed | Synthesis, Anticancer Activity, and Molecular Modeling of New Halogenated Spiro[pyrrolidine-thiazolo-oxindoles] Derivatives |
| title_short | Synthesis, Anticancer Activity, and Molecular Modeling of New Halogenated Spiro[pyrrolidine-thiazolo-oxindoles] Derivatives |
| title_sort | synthesis anticancer activity and molecular modeling of new halogenated spiro pyrrolidine thiazolo oxindoles derivatives |
| topic | spirooxindole 1,3-dipolar cycloaddition eco-friendly chemistry rocs shape alignment lipophilicity anticancer activity |
| url | https://www.mdpi.com/2076-3417/10/6/2170 |
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