4290-78-2

Upstream product

• 106-93-4 ethylene dibromide 
• 91-56-5 indole-2,3-dione 
• 107-04-0 1-Bromo-2-chloroethane 
• 1609115-01-6 C₁₀H₁₂BrNO 

Downstream Products

• 1410051-39-6 C₁₇H₁₂BrN₅O₃S 

Relevant academic research and scientific papers

Synthesis of 6-aminopropyl-6H-indolo[2,3-b]quinoxaline derivatives

A series of 6-(3-aminopropyl)-6H-indolo[2,3-b]quinoxalines were synthesized with high yields by the reaction of 6-(3-chloropropyl)-6H-indolo[2,3-b] quinoxaline and corresponding amines in presence of tetrabutylammonium iodide in boiling toluene or dimethylformamide at room temperature. It was found that boiling of 6-(3-chloropropyl)-6H-indolo[2,3-b]quinoxaline in acetone with sodium iodide or in acetic acid lead to intramolecular cyclization product.

Synthesis of Ethylene Tethered Isatin-Coumarin Hybrids and Evaluation of Their in vitro Antimycobacterial Activities

A series of novel isatin-coumarin derivatives tethered through ethylene were designed, synthesized, and evaluated for their in vitro antimycobacterial activities against Mycobacterium tuberculosis (MTB) H37Rv and multidrug-resistant tuberculosis (MDR-TB). All hybrids exhibited potential antimycobacterial activities against MTB H37Rv and MDR-TB with minimum inhibitory concentration (MIC) ranging from 32 to 256?μg/mL. In particular, the hybrid 4h (MIC: 50 and 32?μg/mL) was most active against MTB H37Rv and MDR-TB strains, which was 2 and >4 folds more potent than the first-line antitubercular agents rifampicin (MIC: 64?μg/mL) and isoniazid (MIC: >128?μg/mL) against MDR-TB, warrant further optimization.

Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines

New 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines were synthesized with high yields using bromoethylisatin and 6-(2-bromoethyl)-6H-indolo[2,3-b]quinoxaline as intermediates. These compounds were screened for the cytotoxicity, antiviral activity and interferon inducing ability. It was shown, that tested 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines are low toxic potent interferon inducers and antivirals. Morpholine and 4-methyl-piperidine derivatives appeared as the most active antivirals and the least cytotoxic in the investigated series.

Azide-alkyne cycloaddition en route to novel 1H-1,2,3-triazole tethered isatin conjugates with in vitro cytotoxic evaluation

1H-1,2,3-triazole tethered isatin conjugates have been synthesized and evaluated for cytotoxicity on four human cancer cell lines. The results revealed 5a, 5c, 5e and 5n proved to be twice as potent as 5-fluorouracil on THP-1 cell line with 5a and 5c being most active exhibiting IC50 values of 1 against all cell lines except Caco-2. Activity profiles showed dependence on the substituents on isatin rings with a preference for hydrogen while a strong electron withdrawing fluoro as well as nitro substituents on either ring decreased the anticancer activity.

Design, synthesis and in vitro anti-mycobacterial activities of homonuclear and heteronuclear bis-isatin derivatives

A series of novel homonuclear and heteronuclear bis-isatin derivatives tethered through ethylene were designed, synthesized and evaluated for their in vitro anti-mycobacterial activities against MTB H37Rv and MDR-TB. All hybrids exhibited potential anti-mycobacterial activities against MTB H37Rv and MDR-TB with MIC ranging from 16 to 256 μg/mL. In particular, the heteronuclear bis-isatin 4i (MIC: 25 and 16 μg/mL) was most active against MTB H37Rv and MDR-TB strains, and could act as a lead for further optimization.

Design, synthesis and anti-mycobacterial activity evaluation of benzofuran-isatin hybrids

Herein we report the design and synthesis of a series of novel benzofuran-isatin hybrids, and in vitro evaluation of their anti-mycobacterial activity against both drug-susceptible and multi-drug resistant (MDR) Mycobacterium tuberculosis (MTB) strains. I

Rapid assembly of heterocycle grafted macrocycles via tandem one-pot double 1,3-dipolar cycloaddition reaction

Synthesis of triazole linked macrocycles grafted with glycospiroheterocycle was accomplished by stereo- and regioselective tandem double 1,3-dipolar cycloaddition (1,3-DC) reaction. By this method we could construct complex chiral macrocycles in good yields from the easily available starting materials and we could achieve the synthesis of two heterocyclic rings involving simultaneous formation of five bonds in one-pot reaction. The structures of the macrocycles were confirmed by spectroscopic methods and single crystal XRD. This journal is

Design, Synthesis and in vitro Antimycobacterial Activities of Isatin-1,2,3-triazole-moxifloxacin Hybrids

A new class of isatin-1,2,3-triazole-moxifloxacin (MXFX) hybrids 5a–j was designed, synthesized, and screened for their in vitro antimycobacterial activities against Mycobacterium tuberculosis H37Rv and MDR-TB. All the synthesized hybrids (MIC: 0.10–0.78?μg/mL) exhibited excellent activities against MTB H37Rv and MDR-TB, in spite of none of them were more potent than the parent MXFX (MIC: 0.10 and 0.12?μg/mL). Against MTB H37Rv, the most active 5f (MIC: 0.10?μg/mL) was comparable with MXFX and 4 times more potent than RIF (MIC: 0.39?μg/mL). Against MDR-TB, all hybrids were more active than RIF (MIC: 32?μg/mL) and INH (MIC: >128?μg/mL). In particular, hybrid 5e (MIC: 0.10?μg/mL) was comparable with MXFX and 256 and >1,024 times more potent than RIF and INH. Both conjugates 5e and 5f warrant further investigations.

Isatin-derived azoles as new potential antimicrobial agents: Design, synthesis and biological evaluation

Novel antibiotics are forced to be developed on account of multidrug-resistant bacteria with serious threats to human health. This work developed isatin-derived azoles as new potential antimicrobial agents. Bioactive assay revealed that isatin hybridized 1,2,4-triazole 7a exhibited excellent inhibitory activity against E. coli ATCC 25,922 with an MIC value of 1 μg/mL, which was 8-fold more potent than reference drug norfloxacin. The active molecule 7a possessed the ability to kill some bacteria and fungi as well as displayed low propensity to induce resistance towards E. coli ATCC25922. Preliminary mechanism investigation indicated that hybrid 7a might block deoxyribonucleic acid (DNA) replication by intercalating with DNA and possibly interacting with DNA polymerase III, thus exerting its antimicrobial potency.

Design, synthesis, and biological evaluation of isatin-indole-3-carboxaldehyde hybrids as a new class of xanthine oxidase inhibitors

A novel series of triazole-linked isatin-indole-3-carboxaldehyde hybrids based on the febuxostat skeleton and its binding site interactions were rationally designed and synthesized as potential xanthine oxidase inhibitors. Among the synthesized hybrids, A19 showed the most potent xanthine oxidase inhibition (IC50 = 0.37 μM) with the mixed-type inhibitory scenario. Structure–activity relationship studies revealed that methoxy (OCH3) substitution on position 5 of the isatin nucleus and a two-carbon distance between isatin and the triazole moiety is most tolerable for the inhibitory potential. Various binding interactions of A19 with the binding site of xanthine oxidase are also streamlined by molecular docking studies, which showcase the favorable binding pattern for xanthine oxidase inhibition by the hybrid. Furthermore, molecular dynamic studies were performed that suggest the stability of the enzyme–hybrid complex. Overall, the study suggests that hybrid A19 can act as an effective hit lead for further development of potent xanthine oxidase inhibitors.