78599-49-2Relevant academic research and scientific papers
Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: Trigonoine B
Nishiyama, Takashi,Hamada, Erina,Ishii, Daishi,Kihara, Yuuto,Choshi, Nanase,Nakanishi, Natsumi,Murakami, Mari,Taninaka, Kimiko,Hatae, Noriyuki,Choshi, Tominari
, p. 730 - 736 (2021/04/12)
The first total synthesis of the pyrrolo[2,3-c]quinoline alkaloid trigonoine B (1) was accomplished via a six-step sequence involving the construction of an N-substituted 4-aminopyrrolo[2,3-c]quinoline framework via electrocyclization of 2-(pyrrol-3-yl)benzene containing a carbodiimide moiety as a 2-azahexatriene system. The employed six-step sequence afforded trigonoine B (1) in 9.2% overall yield. The described route could be employed for the preparation of various N-substituted 4-aminopyrroloquinolines with various biological activities.
Pyochelin Biosynthetic Metabolites Bind Iron and Promote Growth in Pseudomonads Demonstrating Siderophore-like Activity
Kaplan, Anna R.,Musaev, Djamaladdin G.,Wuest, William M.
, p. 544 - 551 (2021/03/03)
Pseudomonads employ several strategies to sequester iron vital for their survival including the use of siderophores such as pyoverdine and pyochelin. Similar in structure but significantly less studied are pyochelin biosynthetic byproducts, dihydroaeruginoic acid, aeruginoic acid, aeruginaldehyde (IQS), and aeruginol, along with two other structurally related molecules, aerugine and pyonitrins A-D, which have all been isolated from numerous Pseudomonad extracts. Because of the analogous substructure of these compounds to pyochelin, we hypothesized that they may play a role in iron homeostasis or have a biological effect on other bacterial species. Herein, we discuss the physiochemical evaluation of these molecules and disclose, for the first time, their ability to bind iron and promote growth in Pseudomonads.
Synthesis and Investigation of the Abiotic Formation of Pyonitrins A-D
Aniebok, Victor,Lee, Hsiau-Wei,Macmillan, John B.,Shingare, Rahul D.
, (2020/02/22)
Pyonitrins A-D are recently isolated natural products from the insect-associated Pseudomonas protegens strain, which were isolated from complex fractions that exhibited antifungal activity via an in vivo murine candidiasis assay. Genomic studies of Pseudomonas protegens suggested that pyonitrins A-D are formed via a spontaneous nonenzymatic reaction between biosynthetic intermediates of two well-known natural products pyochelin and pyrrolnitrin. Herein we have accomplished the first biomimetic total synthesis of pyonitrins A-D in three steps and studied the nonenzymatic formation of the pyonitrins using 15N NMR spectroscopy.
Discovery of Marinoquinolines as Potent and Fast-Acting Plasmodium falciparum Inhibitors with in Vivo Activity
Aguiar, Anna Caroline Campos,Panciera, Michele,Simao Dos Santos, Eric Francisco,Singh, Maneesh Kumar,Garcia, Mariana Lopes,De Souza, Guilherme Eduardo,Nakabashi, Myna,Costa, José Luiz,Garcia, Célia R.S.,Oliva, Glaucius,Correia, Carlos Roque Duarte,Guido, Rafael Victorio Carvalho
, p. 5547 - 5568 (2018/06/18)
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.
New class of antitubercular compounds: Synthesis and anti-tubercular activity of 4-substituted pyrrolo[2,3-c]quinolines
Akula, Mahesh,Sridevi, Jonnalagadda Padma,Yogeeswari,Sriram,Bhattacharya, Anupam
, p. 811 - 819 (2014/05/20)
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.]
Biomimetic synthesis and biological evaluation of aplidiopsamine A
Panarese, Joseph D.,Lindsley, Craig W.
, p. 5808 - 5810 (2013/01/15)
The first total synthesis of Aplidiopsamine A, a rare 3H-pyrrolo[2,3-c] quinoline alkaloid from the Aplidiopsis confluata, has been achieved following the proposed biosynthesis. This biomimetic synthesis requires only five steps and proceeds in 20.8% overall yield. Biological evaluation across large panels of discrete molecular targets identified that Aplidiopsamine A is a highly selective PDE4 inhibitor, a target for numerous CNS disorders.
Divergent total synthesis of the natural antimalarial marinoquinolines A, B, C, e and unnatural analogues
Schwalm, Cristiane Storck,Correia, Carlos Roque D.
, p. 4836 - 4840 (2012/09/07)
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.
Total synthesis of rhazinilam: Axial to point chirality transfer in an enantiospecific Pd-catalyzed transannular cyclization
Gu, Zhenhua,Zakarian, Armen
supporting information; experimental part, p. 4224 - 4227 (2010/11/17)
Figure Presented. A total synthesis of rhazinilam based on a transannular cyclization strategy is described. Using a Heck reaction, the axial chirality of a halogenated 13-membered lactam can be exploited to create the quaternary chiral stereogenic center in the target molecule with high enantiospecificity.
Synthesis of pyrrolnitrin and related halogenated phenylpyrroles
Morrison, Matthew D.,Hanthorn, Jason J.,Pratt, Derek A.
supporting information; experimental part, p. 1051 - 1054 (2009/07/18)
A general approach to halogenated arylpyrroles, including the antifungal natural product pyrrolnitrin, is described using newly synthesized halogenated pyrroles and 2,6-disubstituted nitrobenzenes or 2,6-disubstituted anilines.
