Vinyl azides in heterocyclic synthesis. Part 8. Synthesis of the naturally occurring phosphodiesterase inhibitors PDE-I and PDE-II

Bolton, R.; Moody, Christopher J.; Rees, Charles W.; Tojo, Gabriel

doi:10.1039/p19870000931

Cited by 39 publications

(8 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…49 It is also useful in the synthesis of a range of indole natural products such as coenzyme PQQ, 50 and highly substituted indoles, as exemplied by the synthesis of the pyrroloindoles PDE-I and PDE-II, proceeding through two sequential Hemetsberger reactions (Scheme 25). 51 Despite the potential hazards associated with the use of azides, the Hemetsberger reaction is amenable to scale up and has been carried on 90 g scale in Cook's synthesis of roeharmine. 52 The Hemetsberger reaction can be carried out under transition metal catalysis, using either the azides 53 or azirines 54 as starting materials.…”

Section: The Hemetsberger Indole Synthesismentioning

confidence: 99%

Indole synthesis – something old, something new

2013

Self Cite

View full text Add to dashboard Cite

Indoles, both naturally occurring and synthetic, exhibit wide-ranging biological activity. Unusual and complex molecular architectures occur among their natural derivatives. As a result, this important ring system continues to attract attention from the international chemical community, and new methodologies for the construction of this ever relevant heteroaromatic ring continue to be developed.Unfortunately, many methods frequently start from ortho-substituted anilines, thereby greatly restricting the availability of starting materials. A more general approach would start from a mono-functionalized arene such as an aniline or halobenzene, followed by cyclization with C-C or C-N bond formation to an unactivated C-H bond. Such methods are the subject of this perspective.

show abstract

Section: The Hemetsberger Indole Synthesismentioning

confidence: 99%

Indole synthesis – something old, something new

2013

Self Cite

View full text Add to dashboard Cite

show abstract

“…Examples of successfully completed syntheses which involve such reactions as a key step include: the coenzyme PQQ, 1 and phosphodiesterase inhibitors PDE-I and -II. 2 Later independent work saw the completion of the synthesis of the alkaloids murrayaquinone-B, 3 lennoxamine, 4 indolactam V 5 and BE10988 (Fig. 1).…”

Section: Researchmentioning

confidence: 99%

Professor Christopher J. Moody

Moody¹

2001

J. Chem. Soc., Perkin Trans. 1

Self Cite

View full text Add to dashboard Cite

“…The Hemetsberger reaction was chosen as the synthetic preparation method for the designated indole compounds since it readily forms derivatives of 2-carboxyindoles from aromatic or heterocyclic aldehydes. [30][31][32] The position 2 was chosen as the first location on the indole ring for the preparation of the first set of compounds. 4,6-Dimethoxyindole-2-carbaldehyde 33 was prepared by reduction and oxidation of methyl 4,6-dimeth oxyindole-2-carboxylate, respectively.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterisation of novel 4,6-dimethoxyindole-7- and -2-thiosemicarbazone derivatives: Biological evaluation as antioxidant and anticholinesterase candidates

Bingül

2019

Journal of Chemical Research

View full text Add to dashboard Cite

Two sets of novel indole-based thiosemicarbazone systems 8a–d and 9a–d are prepared by the Schiff base condensation reaction of indole carbaldehydes 4 and 6 with a range of thiosemicarbazides 7a–d in high yields and purity. The antioxidant properties of the synthesised compounds 8a–d and 9a–d are determined by employing three different assays, namely 2,2-diphenyl-1-picrylhydrazyl hydrate–free radical scavenging, ABTS [2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)] cationic radical decolarization and cupric ion reducing antioxidant capacity. The anticholinesterase properties of the products are investigated by acetylcholinesterase and butyrylcholinesterase enzyme inhibition assays. The methyl-substituted compounds 8b and 9b display the highest inhibition for the ABTS assay and absorbance values for the cupric ion reducing antioxidant capacity assay, while compound 9c shows the best activity for 2,2-diphenyl-1-picrylhydrazyl hydrate assay. Moderate inhibition of acetylcholinesterase and butyrylcholinesterase is determined in the case of compound 8b.

show abstract

Vinyl azides in heterocyclic synthesis. Part 8. Synthesis of the naturally occurring phosphodiesterase inhibitors PDE-I and PDE-II

Cited by 39 publications

References 4 publications

Indole synthesis – something old, something new

Indole synthesis – something old, something new

Professor Christopher J. Moody

Synthesis and characterisation of novel 4,6-dimethoxyindole-7- and -2-thiosemicarbazone derivatives: Biological evaluation as antioxidant and anticholinesterase candidates

Contact Info

Product

Resources

About