Facile one-pot synthesis,antiproliferative evaluation and structure-activity relationships of 3-amino-1H-indoles and 3-amino-1H-7-azaindoles |
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| Institution: | 1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy (girls), Al-Azhar University, Nasr City, Cairo, Egypt;2. Department of Organic Chemistry, Faculty of Science, Ain Shams University, Abbassia, 11566 Cairo, Egypt;1. IDD Medicinal Chemistry, Sanofi, 153 Second Avenue, Waltham MA 02451, United States;2. Oncology Biology, Sanofi, 270 Albany Street, Cambridge MA 02139, United States;3. Oncology Biochemistry, Sanofi, 270 Albany Street, Cambridge MA 02139, United States;4. Oncology Pharmacology, Sanofi, 640 Memorial Drive, Cambridge MA 02139, United States;1. Pharmaceutical Medicinal Chemistry and Drug Design Department, Faculty of Pharmacy (Boys), Al-Azhar University, Nasr City 11884, Cairo, Egypt;2. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Heliopolis University for Sustainable Development, Cairo, Egypt;1. Medicinal &Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre (NRC ID: 60014618), Dokki, Giza 12622, Egypt;2. Center for Biomaterials, Korea Institute of Science & Technology (KIST School), Seoul, Seongbuk-gu 02792, Republic of Korea;3. University of Science & Technology (UST), Daejeon, Yuseong-gu 34113, Republic of Korea;4. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Modern University of Technology and Information (MTI), Cairo 12055, Egypt;5. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Ahram Canadian University, Giza 12566, Egypt;6. Chemical Kinomics Research Center, Korea Institute of Science and Technology, Seoul, Republic of Korea |
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| Abstract: | A highly efficient method has been developed for the one-pot synthesis of substituted 3-amino-1H-indole and 3-amino-1H-7-azaindole derivatives starting from ethyl 2-cyanophenylcarbamate/ethyl 3-cyanopyridin-2-ylcarbamate, and α-bromoketones in good to excellent yields. All newly synthesized analogues were screened for their antiproliferative activities against four cancer cell lines. The most promising compound 8v demonstrated 13-, 5-, and 1.4-fold improvement compared to fluorouracil in inhibiting HeLa, HepG2, and MCF-7 cell proliferation with IC50 values of 3.7, 8.0, and 19.9 μM, respectively. Furthermore, 8v induced significant cell cycle arrest at the G2/M phase in HeLa cell lines via a concentration-dependent manner. These encouraging findings indicate that the common 3-amino-1H-7-azaindole is a very favorable scaffold for the design of novel anticancer small-molecule drugs. |
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| Keywords: | 3-amino-1H-indoles 3-amino-1H-7-azaindoles One-pot synthesis Antiproliferative activity |
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