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Upstream product

• 78105-37-0 2-chloro-3-nitroquinoline 
• 128676-84-6 (2-chloroquinolin-3-yl)boronic acid 
• 233770-18-8 2-formyl-3-(o-nitrophenyl)-1-tosylpyrrole 
• 1589-82-8 phenylmagnesium bromide 
• 577-19-5 2-nitrophenyl bromide 
• 1033282-26-6 3-(2-nitrophenyl)-1-(triisopropylsilyl)-1H-pyrrole 
• 52636-03-0 3-(2-nitrophenyl)-1H-pyrrole 
• 24347-60-2 2,5-dimethylhexane-2,3-diol 
• 1126425-85-1 2-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline 
• 615-36-1 2-bromoaniline 
• 365-33-3 2-nitrobenzenediazonium tetrafluoroborate 
• 122-78-1 phenylacetaldehyde 
• 78599-49-2 3-(2'-aminophenyl)pyrrole 
• 1393935-90-4 C₁₃H₁₄N₂O₄ 

Relevant academic research and scientific papers

Extending the utility of the bartoli indolization: Synthesis of marinoquinolines C and e

A short synthesis of marinoquinolines C and E has been achieved. The synthetic route involves an ipso nitration of an electron-deficient boronic acid, the first example of a Bartoli indolization on a nitroquinoline and Suzuki coupling between 2-chloropyrroloquinoline and two separate MIDA boronates. Georg Thieme Verlag Stuttgart · New York.

Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties

A catalytic domino reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a broad range of starting nitroarenes involving several redox processes. Not only is this a sustainable, step-economical as well as air- and moisture-tolerant method, but also it is worth highlighting that the waste byproduct generated in the first step of the sequence is recycled and incorporated in the final target molecule, improving the overall synthetic efficiency. Moreover, selected indoloquinoxalines have been photophysically characterized in cyclohexane and toluene with exceptional fluorescence quantum yields above 0.7 for the alkyl derivatives.

Total Syntheses of the 3 H-Pyrrolo[2,3- c]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway

Compounds 1-6 and 11 representing key members of the marinoquinoline family of natural products, together with the related marine alkaloid aplidiopsamine A (12), have been synthesized using various combinations of palladium-catalyzed Ullmann cross-coupling and reductive cyclization processes involving a C3-arylated pyrrole as the common intermediate. These natural products have been characterized by single-crystal X-ray analyses and evaluated as inhibitors of acetylcholinesterase (AChE) with congener 2 proving to be the most active.

Discovery of Marinoquinolines as Potent and Fast-Acting Plasmodium falciparum Inhibitors with in Vivo Activity

We report the discovery of marinoquinoline (3H-pyrrolo[2,3-c]quinoline) derivatives as new chemotypes with antiplasmodial activity. We evaluated their inhibitory activities against P. falciparum and conducted a structure-activity relationship study, focusing on improving their potency and maintaining low cytotoxicity. Next, we devised quantitative structure-activity relationship (QSAR) models, which we prospectively validated, to discover new analogues with enhanced potency. The most potent compound, 50 (IC503d7 = 39 nM; IC50K1 = 41 nM), is a fast-acting inhibitor with dual-stage (blood and liver) activity. The compound showed considerable selectivity (SI > 6410), an additive effect when administered in combination with artesunate, excellent tolerability in mice (all mice survived after an oral treatment with a 1000 mg/kg dose), and oral efficacy at 50 mg/kg in a mouse model of P. berghei malaria (62% reduction in parasitemia on day 5 postinfection); thus, compound 50 was considered a lead compound for the discovery of new antimalarial agents.

Development of a Br?nsted acid-promoted arene-ynamide cyclization toward the total syntheses of marinoquinolines A and C and aplidiopsamine A

(Chemical Equation Presented) A Br?nsted acid-promoted arene-ynamide cyclization has been developed to construct the 3H-pyrrolo[2,3-c]quinolines. This reaction consists of the generation of a highly reactive keteniminium intermediate from arene-ynamide activated by a Br?nsted acid and electrophilic aromatic substitution reaction to give arene-fused quinolines in high yields. This methodology enabled facile access to marinoquinolines A and C and aplidiopsamine A.

New class of antitubercular compounds: Synthesis and anti-tubercular activity of 4-substituted pyrrolo[2,3-c]quinolines

Modified synthesis and antitubercular activity of 4-substituted pyrrolo[2,3-c]quinolines are reported. Some of the compounds showed significant antitubercular activity, when compared to some of the existing antitubercular drugs. A compound with an imidazole moiety at position 4 shows the highest activity and least toxicity. Graphical abstract: [Figure not available: see fulltext.]

Divergent total synthesis of the natural antimalarial marinoquinolines A, B, C, e and unnatural analogues

A new synthetic route to marinoquinolines was developed, allowing the synthesis of several structurally related compounds from a common key intermediate. Four natural marinoquinolines (A, B, C and E) and nine unnatural new analogues were prepared by this strategy, which features a Heck-Matsuda reaction in pure water and the Pictet-Spengler reaction as key steps.

Concise total syntheses of Marinoquinolines A-C

The first concise total syntheses of pyrroloquinoline natural products, Marinoquinolines A-C, have been achieved in six linear steps from commercially available starting materials. The key steps were a reaction between (p-tolylsulfonyl)methylisocyanide (TosMIC) and α, β-unsaturated ester under basic condition to prepare the pyrrole moiety and Morgen-Walls reaction to construct quinoline ring.