A New Synthesis of Indole-3-aldehydes. The Reaction of Hexamethylenetetramine with Some Mannich Bases

Snyder, H. R.; Swaminathan, S.; Sims, Homer J.

doi:10.1021/ja01140a034

Cited by 29 publications

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“…N ‐Chloroacetyl sulfonamide intermediates 10a–e were prepared as previously reported by stirring a mixture of the appropriate sulfonamide and chloroacetyl chloride in dimethylformamide, the intermediate thiazolidinones 11a–e were also prepared according to the reported procedures by reacting 10a–e with ammonium thiocyanate and refluxing in absolute ethanol . Additionally, 1 H ‐indole‐3‐carbaldehyde 13 was prepared as reported via Vilsmeir Haack formylation of the commercially available 1 H ‐indole 12 using phosphorous oxychloride (POCl 3 ) and dimethylformamide (DMF) …”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and molecular docking of novel indole scaffold‐based VEGFR‐2 inhibitors as targeted anticancer agents

Roaiah

Ghannam

Ali

et al. 2018

Archiv der Pharmazie

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A series of new indole derivatives 1-18 was synthesized and tested for their cytotoxic activity on a panel of 60 tumor cell lines. Additionally, molecular docking was carried out to study their binding pattern and binding affinity in the VEGFR-2 active site using sorafenib as a reference VEGFR-2 inhibitor. Based on the molecular docking results, compounds 5a, 5b, 6, 7, 14b, 18b, and 18c were selected to be evaluated for their VEGFR-2 inhibitory activity. Compound 18b exhibited a broad-spectrum antiproliferative activity on 47 cell lines, with GI % ranging from 31 to 82.5%. Moreover, compound 18b was the most potent VEGFR-2 inhibitor with an IC value of 0.07 μM, which is more potent than that of sorafenib (0.09 μM). A molecular docking study attributed the promising activity of this series to their hydrophobic interaction with the VEGFR-2 binding site hydrophobic side chains and their hydrogen bonding interaction with the key amino acids Glu885 and/or Asp1046.

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Section: Resultsmentioning

confidence: 99%

Design, synthesis, and molecular docking of novel indole scaffold‐based VEGFR‐2 inhibitors as targeted anticancer agents

Roaiah

Ghannam

Ali

et al. 2018

Archiv der Pharmazie

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“…However, for amidic IP compounds 7a − e , these conditions (like those of Riemer−Tiemann) proved inefficient or offered only low yields of formyl compounds (degradation or yields below 10%, data not shown). Given these disappointing results, we decided to explore Duff formylation (hexamethylenetetramine (HMTA) in acetic acid or TFA), already used on several heterocyclic systems and found to be efficient in IP series (18% to 29% isolated yield of formyl compounds).…”

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confidence: 99%

New Opportunities with the Duff Reaction

et al. 2008

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Carbon‐Carbon Alkylations with Amines and Ammonium Salts

Brewster

Eliel

2011

Organic Reactions

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This chapter is a review of those reactions of compounds containing labile amino groups in which a carbon‐carbon bond is formed by amine replacement as, for example, in the alkylation of diethyl malonate by 1‐dimethylamino‐3‐butanone. Attention has been given primarily to reactions of amines prepared by the Mannich reaction (Mannich bases), but for comparison, analogous reactions of simpler quaternary ammonium salts have been included.

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A New Synthesis of Indole-3-aldehydes. The Reaction of Hexamethylenetetramine with Some Mannich Bases

Cited by 29 publications

References 0 publications

Design, synthesis, and molecular docking of novel indole scaffold‐based VEGFR‐2 inhibitors as targeted anticancer agents

Design, synthesis, and molecular docking of novel indole scaffold‐based VEGFR‐2 inhibitors as targeted anticancer agents

New Opportunities with the Duff Reaction

Carbon‐Carbon Alkylations with Amines and Ammonium Salts

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