Please use this identifier to cite or link to this item: https://hdl.handle.net/11147/11160
Title: Synthesis of novel coumarin-1,2,3-triazole hybrids as potential anticancer agents
Other Titles: Potansiyel antikanser ajanı olabilecek yeni kumarin-1,2,3-triazol hibritlerinin sentezlenmesi
Authors: Çağır, Ali
Akman, Bora
Izmir Institute of Technology
Keywords: Coumarin
Anticancer agent
Triazoles
Coumarin-triazole hybrid
Issue Date: Jul-2021
Publisher: Izmir Institute of Technology
Source: Akman, B. (2021). Synthesis of novel coumarin-1,2,3-triazole hybrids as potential anticancer agents. Unpublished master's thesis, İzmir Institute of Technology, İzmir, Turkey
Abstract: Coumarin and triazole derivatives have been extracted from plants, seeds and roots for ages in traditional methods. As the science advances, unknown profits of biologically active compounds have been investigating by researchers in modern laboratories. Extracts of natural sources containing coumarin and triazole derivatives were found to be potential natural medicines. The organic structures of these molecules bear extraordinary biological activities such as inflammatory activity, anti-HIV activity, treatment of cold and rheumatism and anticancer activity. In this study, attemps toward the synthesis of coumarin-triazole hybrids will be presented. At first attempt, starting from 2-amino-5-chlorophenol, coumarin-triazole hybrids were tried to be obtained through ynone intermediates, yet the experiments on acquiring corresponding ynone intermediates were failed. As second approach, 4-iodocoumarin and 4-bromocoumarin derivatives were tried to be synthesized from 4-hydroxycoumarin derivative that was acquired from acetyl salicylic acid, and the attempts were failed again. As an alternative, 4-tosylcoumarin derivative was used as pseudo halogenated coumarin derivative with triazole derivatives that were prepared starting from 4-chlorobenzyl azide. However, the failure was witnessed after all trials. In further trials, obtaining an internal alkyne as Sonogashira product from 4-tosylcoumarin derivative was the first step of another approach to produce desired hybrid structures. Unfortunately, in the second step a click chemistry between Sonogashira product and 4-cholorobenzyl azide was failed to form corresponding hybrid structures. Finally, possible Heck reaction was studied between coumarin derivative and 5-iodo-1,2-disubstituted-1,2,3-triazole derivative, that was also failed to obtain desired coumarin-triazole hybrid.
Kumarin ve triazol türevleri, asırlardır geleneksel yollarla çeşitli bitkilerden, bitkilerin tohumlarından ve köklerinden özütlenmektedir. Bilim ilerledikçe, bu biyolojik olarak aktfi olan bileşiklerin üzerine yapılan incelemeler de bilim insanları tarafından modern laboratuvarlara taşınmıştır. Kumarin ve triazol türevleri içeren doğal bileşiklerin özütleri doğal ilaçlar olarak göze çarpmaktadır. Bu olağanüstü bileşiklerin soğuk algınlığı ve romatizma tedavilerinde kullanılmalarının yanı sıra ateş düşürücü, iltihap giderici, anti-HIV ve antikanser aktivite de gösterdikleri anlaşılmıştır. Bu çalışmada, kumarin-triazol hibritlerinin sentezlenmesi için yapılan çalışmalar sunulacaktır. İlk yaklaşımda, 2-amino-5-klorofenol bileşiğinden yola çıkarak, yinon ara ürünü üzerinden kumarin-triazol hibritleri elde edilmeye çalışılsa da yinon ara ürünü sentezinde başarılı olunamamıştır. İkinci denemede, asetil salisilik asit’den üretilen 4-hidroksikumarin türevini 4-iyodokumarin ve 4-bromokumarin türevlerine çevrilmesine çalışılmıştır fakat başarılı olunamamıştır. Alternatif olarak, psödohalojen olarak davranabilen 4-tosilkumarin türevi, 4-klorobenzil kloro’dan sentezlenen triazol türevi ile reaksiyona sokulmuştur ama tüm denemeler başarısızlıkla sonuçlanmıştır. Sonraki denemelerde Sonogashira ürünü olarak elde edilen ve internal bir alkin olan kumarin türevinin 4-klorobenzil azit ile olan reaksiyonundan arzulanan kumarin-triazol türevi elde edilemememiştir. Son olarak, metil 2-okso-2H-kromen-3-karboksilat ile 5-iyodo-1,2-disübtütient-1,2,3-triazole türevi arasında çalışılan Heck reaksiyonu ile kumarin-triazol türevleri elde edilmeye çalışılsa da denemeler sonuç vermemiştir.
Description: Thesis (Master)--Izmir Institute of Technology, Chemistry, Izmir, 2021
Includes bibliographical references (leaves. 49-54)
Text in English; Abstract: Turkish and English
URI: https://hdl.handle.net/11147/11160
Appears in Collections:Master Degree / Yüksek Lisans Tezleri

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