64566-93-4

Usage

Structure

A derivative of pyrrole, a five-membered aromatic heterocycle, with two chlorine atoms attached to the 4 and 5 positions and a carbonyl chloride group attached to the 2 position

Usage

A versatile building block in organic synthesis for the preparation of various pyrrole derivatives and other biologically active compounds, and a valuable intermediate for the production of pharmaceuticals, agrochemicals, and materials with potential industrial applications

Reactivity

A reactive chemical that requires careful handling

Potential hazards

Potentially hazardous due to its reactivity

Upstream product

• 634-97-9 pyrrole-2-carboxyl acid 
• 39209-94-4 4, 5-dichloro-1H-pyrrole-2-carboxylic acid 
• 1003-29-8 2-pyrrole aldehyde 

Downstream Products

• 1299491-66-9 4,5-dichloro-1H-pyrrole-2-carboxylic acid (3-methoxy-4-prop-2-ynyloxybenzyloxy)amide 

Relevant academic research and scientific papers

Discovery of Benzothiazole Scaffold-Based DNA Gyrase B Inhibitors

Bacterial DNA gyrase and topoisomerase IV control the topological state of DNA during replication and are validated targets for antibacterial drug discovery. Starting from our recently reported 4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-based DNA gyrase B inhibitors, we replaced their central core with benzothiazole-2,6-diamine scaffold and interchanged substituents in positions 2 and 6. This resulted in equipotent nanomolar inhibitors of DNA gyrase from Escherichia coli displaying improved inhibition of Staphylococcus aureus DNA gyrase and topoisomerase IV from both bacteria. Compound 27 was the most balanced inhibitor of DNA gyrase and topoisomerase IV from both E. coli and S. aureus. The crystal structure of the 2-((2-(4,5-dibromo-1H-pyrrole-2-carboxamido)benzothiazol-6-yl)amino)-2-oxoacetic acid (24) in complex with E. coli DNA gyrase B revealed the binding mode of the inhibitor in the ATP-binding pocket. Only some compounds possessed weak antibacterial activity against Gram-positive bacteria. These results provide a basis for structure-based optimization toward dual DNA gyrase and topoisomerase IV inhibitors with antibacterial activity.

Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs

A series of novel analogs of pyrrole alkaloid were designed and synthesized by a facile method and their structures were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). The structure of compound 2a was identified by 2D NMR including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC) and H-H correlation spectrometry (H-H COSY) spectra. Their antifungal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed moderate fungicidal activities in vitro against Alternaria solani, Cercospora arachidicola, Fusarium omysporum, Gibberella zeae and Physalospora piricola at the dosage of 50 μg mL -1. Compound 2a and 3a exhibited good activities against P. piricola at low dosage.