An efficient green approach for the synthesis of benzothiazole‐linked pyranopyrazoles as promising pharmacological agents and docking studies
Benzothiazole‐tethered pyranopyrazoles derivatives were prepared via environmentally favorable conditions, which included eco‐friendly catalyst, ethanol−water solvent, one‐pot reaction, and atom‐ and step‐economy procedures. Excellent yield of the products was observed. Besides, all products were sc...
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| Published in | Journal of heterocyclic chemistry Vol. 58; no. 2; pp. 548 - 557 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Chichester, UK
John Wiley & Sons, Inc
01.02.2021
Wiley Wiley Subscription Services, Inc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0022-152X 1943-5193 |
| DOI | 10.1002/jhet.4194 |
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| Abstract | Benzothiazole‐tethered pyranopyrazoles derivatives were prepared via environmentally favorable conditions, which included eco‐friendly catalyst, ethanol−water solvent, one‐pot reaction, and atom‐ and step‐economy procedures. Excellent yield of the products was observed. Besides, all products were screened for their antimicrobial behavior. From the biological results, it was seen that most of the compounds possessed high to moderate antimicrobial properties. Compound 6a gave prominent antimicrobial property followed by 6d, 6l, and 6n. In addition, computer‐aided studies of the active compounds were also conducted. In this, selected compounds were docked into the intercalation site of DNA of the DNA−gyrase complex. From these results, the highest binding energy of −10.1 kcal/mol was for 6a against DNA−gyrase. This is the first eco‐friendly synthetic method for the preparation of benzothiazole‐pyranopyrazoles and the synthetic effort in this study may serve as a model for additional environmentally benign reactions. The biological results may prompt further studies related to antibiotic drugs. |
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| AbstractList | Benzothiazole-tethered pyranopyrazoles derivatives were prepared via environmentally favorable conditions, which included eco-friendly catalyst, ethanol-water solvent, one-pot reaction, and atom- and step-economy procedures. Excellent yield of the products was observed. Besides, all products were screened for their antimicrobial behavior. From the biological results, it was seen that most of the compounds possessed high to moderate antimicrobial properties. Compound 6a gave prominent antimicrobial property followed by 6d, 6l, and 6n. In addition, computer-aided studies of the active compounds were also conducted. In this, selected compounds were docked into the intercalation site of DNA of the DNA-gyrase complex. From these results, the highest binding energy of -10.1 kcal/mol was for 6a against DNA-gyrase. This is the first eco-friendly synthetic method for the preparation of benzothiazole-pyranopyrazoles and the synthetic effort in this study may serve as a model for additional environmentally benign reactions. The biological results may prompt further studies related to antibiotic drugs. Benzothiazole‐tethered pyranopyrazoles derivatives were prepared via environmentally favorable conditions, which included eco‐friendly catalyst, ethanol−water solvent, one‐pot reaction, and atom‐ and step‐economy procedures. Excellent yield of the products was observed. Besides, all products were screened for their antimicrobial behavior. From the biological results, it was seen that most of the compounds possessed high to moderate antimicrobial properties. Compound 6a gave prominent antimicrobial property followed by 6d , 6l , and 6n . In addition, computer‐aided studies of the active compounds were also conducted. In this, selected compounds were docked into the intercalation site of DNA of the DNA−gyrase complex. From these results, the highest binding energy of −10.1 kcal/mol was for 6a against DNA−gyrase. This is the first eco‐friendly synthetic method for the preparation of benzothiazole‐pyranopyrazoles and the synthetic effort in this study may serve as a model for additional environmentally benign reactions. The biological results may prompt further studies related to antibiotic drugs. Benzothiazole‐tethered pyranopyrazoles derivatives were prepared via environmentally favorable conditions, which included eco‐friendly catalyst, ethanol−water solvent, one‐pot reaction, and atom‐ and step‐economy procedures. Excellent yield of the products was observed. Besides, all products were screened for their antimicrobial behavior. From the biological results, it was seen that most of the compounds possessed high to moderate antimicrobial properties. Compound 6a gave prominent antimicrobial property followed by 6d, 6l, and 6n. In addition, computer‐aided studies of the active compounds were also conducted. In this, selected compounds were docked into the intercalation site of DNA of the DNA−gyrase complex. From these results, the highest binding energy of −10.1 kcal/mol was for 6a against DNA−gyrase. This is the first eco‐friendly synthetic method for the preparation of benzothiazole‐pyranopyrazoles and the synthetic effort in this study may serve as a model for additional environmentally benign reactions. The biological results may prompt further studies related to antibiotic drugs. |
| Author | Raul Garcia, Jarem Wen, Jet‐Chau Venkata Subbaiah, Munagapati Mallikarjuna Reddy, Guda |
| Author_xml | – sequence: 1 givenname: Guda orcidid: 0000-0002-6275-3484 surname: Mallikarjuna Reddy fullname: Mallikarjuna Reddy, Guda email: reddy.organic@gmail.com organization: Ural Federal University, 620002 – sequence: 2 givenname: Jarem orcidid: 0000-0001-9409-288X surname: Raul Garcia fullname: Raul Garcia, Jarem email: nagareddy.organic@gmail.com organization: University of Ponta Grossa – sequence: 3 givenname: Munagapati surname: Venkata Subbaiah fullname: Venkata Subbaiah, Munagapati organization: National Yunlin University of Science & Technology – sequence: 4 givenname: Jet‐Chau surname: Wen fullname: Wen, Jet‐Chau email: wenjc@yuntech.edu.tw organization: National Yunlin University of Science & Technology |
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| Snippet | Benzothiazole‐tethered pyranopyrazoles derivatives were prepared via environmentally favorable conditions, which included eco‐friendly catalyst, ethanol−water... Benzothiazole-tethered pyranopyrazoles derivatives were prepared via environmentally favorable conditions, which included eco-friendly catalyst, ethanol-water... |
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| SubjectTerms | Antibiotics Antiinfectives and antibacterials Biological effects Chemistry Chemistry, Organic Deoxyribonucleic acid DNA Ethanol Physical Sciences Science & Technology |
| Title | An efficient green approach for the synthesis of benzothiazole‐linked pyranopyrazoles as promising pharmacological agents and docking studies |
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