Synthesis of novel artesunate-benzothiophene and artemisinin-benzothiophene derivatives
Natural products are used for the treatment of a variety of diseases for many years. Last decades, design and synthesis of novel biologically active hybrid molecules including natural product is gained big importance due to their unique and new biological properties. In the present study, novel artemisinin-benzothiophene derivatives (12 A-F) are synthesised. Initially, benzothiophene derivatives (4 A-4F) are prepared via the Pd-catalyzed coupling reactions and iodocyclisation reactions. Then, Suzuki-Miyaura coupling reactions were used for the formation of intermediates 6 A-6F (between 64% and 91% yields). Finally, the Steglich esterification reaction between intermediate 6 and artesunate formed the artemisinin-benzothiophene hybrids (9 A-9F) in moderate to excellent yields under very mild reaction conditions. When intermediate 6 was reacted with dihydroartemisinin, product 12 A-12F was also obtained with high yields.[Formula: see text].
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2022 |
|---|---|
| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:36 |
|---|---|
| Enthalten in: |
Natural product research - 36(2022), 20 vom: 22. Okt., Seite 5228-5234 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Ozok, Omruye [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
073790YQ2G |
|---|
| Anmerkungen: |
Date Completed 17.10.2022 Date Revised 17.10.2022 published: Print-Electronic Citation Status MEDLINE |
|---|
| doi: |
10.1080/14786419.2021.1928116 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM325735182 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM325735182 | ||
| 003 | DE-627 | ||
| 005 | 20231225193052.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231225s2022 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1080/14786419.2021.1928116 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1085.xml |
| 035 | |a (DE-627)NLM325735182 | ||
| 035 | |a (NLM)34024198 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Ozok, Omruye |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis of novel artesunate-benzothiophene and artemisinin-benzothiophene derivatives |
| 264 | 1 | |c 2022 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 17.10.2022 | ||
| 500 | |a Date Revised 17.10.2022 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Natural products are used for the treatment of a variety of diseases for many years. Last decades, design and synthesis of novel biologically active hybrid molecules including natural product is gained big importance due to their unique and new biological properties. In the present study, novel artemisinin-benzothiophene derivatives (12 A-F) are synthesised. Initially, benzothiophene derivatives (4 A-4F) are prepared via the Pd-catalyzed coupling reactions and iodocyclisation reactions. Then, Suzuki-Miyaura coupling reactions were used for the formation of intermediates 6 A-6F (between 64% and 91% yields). Finally, the Steglich esterification reaction between intermediate 6 and artesunate formed the artemisinin-benzothiophene hybrids (9 A-9F) in moderate to excellent yields under very mild reaction conditions. When intermediate 6 was reacted with dihydroartemisinin, product 12 A-12F was also obtained with high yields.[Formula: see text] | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Artemisinin | |
| 650 | 4 | |a artesunate | |
| 650 | 4 | |a benzothiophene | |
| 650 | 4 | |a drug design | |
| 650 | 4 | |a natural products | |
| 650 | 4 | |a wormwood plant | |
| 650 | 7 | |a Artemisinins |2 NLM | |
| 650 | 7 | |a Biological Products |2 NLM | |
| 650 | 7 | |a Thiophenes |2 NLM | |
| 650 | 7 | |a benzothiophene |2 NLM | |
| 650 | 7 | |a 073790YQ2G |2 NLM | |
| 650 | 7 | |a Palladium |2 NLM | |
| 650 | 7 | |a 5TWQ1V240M |2 NLM | |
| 650 | 7 | |a Artesunate |2 NLM | |
| 650 | 7 | |a 60W3249T9M |2 NLM | |
| 650 | 7 | |a artemisinin |2 NLM | |
| 650 | 7 | |a 9RMU91N5K2 |2 NLM | |
| 700 | 1 | |a Kavak, Emrah |e verfasserin |4 aut | |
| 700 | 1 | |a Kivrak, Arif |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Natural product research |d 2003 |g 36(2022), 20 vom: 22. Okt., Seite 5228-5234 |w (DE-627)NLM124466303 |x 1478-6427 |7 nnns |
| 773 | 1 | 8 | |g volume:36 |g year:2022 |g number:20 |g day:22 |g month:10 |g pages:5228-5234 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1080/14786419.2021.1928116 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 36 |j 2022 |e 20 |b 22 |c 10 |h 5228-5234 | ||