Highly stereoselective one-pot construction of trisubstituted tetrahydro-β-carboline-fused diketopiperazines: a synthetic route towards cialis analogues

Jida, Mouhamad; Tourwé, Dirk; Ballet, Steven

doi:10.1039/c4ra05981f

Cited by 19 publications

(21 citation statements)

References 39 publications

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“…The synthesised CDPs were subjected to PAMPA model assay to evaluate the passive BBB transport ability. [18] These experimental results revealed that most of the CDPs have the potential to cross the PAMPA, as evaluated over a duration of 4 h. Among all, Oct-N-MePhe (39.4 %), Cha-N-MePhe (35.1 %), 2Nal-N-MePhe (33.7 %), HomoPhe-N-MePhe (26.8 %) and Phe-N-MePhe (20.8 %) have shown the best transportation across BBB over 4 h in PAMPA assay (Figure 8A, [38][39][40][41][42]. These values are similar or better than some of the known drugs such as carbamazepine and propranolol.…”

Section: Biological Barrier Shuttles Cargo Encapsulation and Delivery And Drug Detection 41 Synthetic Cdps As Bbb Shuttlesmentioning

confidence: 96%

Cyclic Dipeptide: A Privileged Molecular Scaffold to Derive Structural Diversity and Functional Utility

2021

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Cyclic dipeptides (CDPs) are the simplest form of cyclic peptides with a wide range of applications from therapeutics to biomaterials. CDP is a versatile molecular platform endowed with unique properties such as conformational rigidity, intermolecular interactions, structural diversification through chemical synthesis, bioavailability and biocompatibility. A variety of natural products with the CDP core exhibit anticancer, antifungal, antibacterial, and antiviral activities. The inherent bioactivities have inspired the development of synthetic analogues as drug candidates and drug delivery systems. CDP plays a crucial role as conformation and molecular assembly directing core in the design of molecular receptors, peptidomimetics and fabrication of functional material architectures. In recent years, CDP has rapidly become a privileged scaffold for the design of advanced drug candidates, drug delivery agents, bioimaging, and biomaterials to mitigate numerous disease conditions. This review describes the structural diversification and multifarious biomedical applications of the CDP scaffold, discusses challenges, and provides future directions for the emerging field.

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Section: Biological Barrier Shuttles Cargo Encapsulation and Delivery And Drug Detection 41 Synthetic Cdps As Bbb Shuttlesmentioning

confidence: 96%

Cyclic Dipeptide: A Privileged Molecular Scaffold to Derive Structural Diversity and Functional Utility

2021

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“…[136] The β-carboline scaffold is also present in numerous active pharmaceuticals including the anti-malarial cipargamin, anti-cancer lurbinectedin and the erectile dysfunction drug tadalafil. [135,[137][138][139][140] Currently, numerous strategies have been outlined for the enantioselective Pictet-Spengler reaction including organo-and transition-metal catalysis. [141,142] However, it was over half a century after the discovery of the chemical transformation before an enzyme catalysed Pictet-Spengler reaction was reported.…”

Section: Biocatalytic Pictet-spengler Reactionsmentioning

confidence: 99%

New Trends and Future Opportunities in the Enzymatic Formation of C−C, C−N, and C−O bonds

et al. 2021

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Organic chemistry provides society with fundamental products we use daily. Concerns about the impact that the chemical industry has over the environment is propelling major changes in the way we manufacture chemicals. Biocatalysis offers an alternative to other synthetic approaches as it employs enzymes, Nature's catalysts, to carry out chemical transformations. Enzymes are biodegradable, come from renewable sources, operate under mild reaction conditions, and display high selectivities in the processes they catalyse. As a highly multidisciplinary field, biocatalysis benefits from advances in different areas, and developments in the fields of molecular biology, bioinformatics, and chemical engineering have accelerated the extension of the range of available transformations (E. L. Bell et al., Nat. Rev. Meth. Prim. 2021, 1, 1-21). Recently, we surveyed advances in the expansion of the scope of biocatalysis via enzyme discovery and protein engineering (J. R. Marshall et al., Tetrahedron 2021, 82, 131926). Herein, we focus on novel enzymes currently available to the broad synthetic community for the construction of new CÀ C, CÀ N and CÀ O bonds, with the purpose of providing the non-specialist with new and alternative tools for chiral and sustainable chemical synthesis.

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“…Jida et al. reported a Ugi‐multicomponent reaction coupled with Pictet‐Spengler reaction strategy for the synthesis of diversely subsituted library of tetrahydro‐β‐carboline fused diketopiperazines (Scheme ) . Synthesis started with a Ugi multicomponent reaction of N 2 ‐Boc‐ L ‐tryptophan primary amines 309 , formaldehyde and tert ‐butylcyanide in methanol to obtain a dipeptide framework.…”

Section: β‐Carboline Fused Heterocycles Synthesized Via Post‐pictet‐smentioning

confidence: 99%

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Singh

Kumar

Patil³

et al. 2020

Adv Synth Catal

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Pictet-Spengler reaction is a typical condensation reaction of β-arylethylamine or Tryptamine with an aldehyde or ketone followed by ring closure to generate tetrahydroisoquinoline (THIQ) and Tetrahydro-β-carboline (THβC), respectively. Both these key skeletons represent huge range of structurally diverse naturally occurring isoquinoline and indole alkaloids. Nature has synthesized structurally complex Reserpine, Ajmalicine as well as other related alkaloids using various biosynthetic pathways via Pictet-Spengler reaction followed by post-Pictet-Spengler cyclization (PPSC) stratergy. This biosynthetic process is the short and reliable method to access diverse range of polycyclic heterocycles. Over the period of last sixty years, several researchers have synthesized complex alkaloids without highlighting the synthetic utility of the post-Pictet-Spengler cyclization strategy. We summarized the synthesis of numerous natural products and related natural product inspired heterocyclic scaffolds which follow the PPSC strategy to demonstrate its usefulness for the construction of diverse compound collection.

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Highly stereoselective one-pot construction of trisubstituted tetrahydro-β-carboline-fused diketopiperazines: a synthetic route towards cialis analogues

Abstract: A facile and efficient synthetic method for the stereoselective preparation of trisubstituted tetrahydro-β-carboline-fused diketopiperazine derivatives is reported.

Cited by 19 publications

References 39 publications

Cyclic Dipeptide: A Privileged Molecular Scaffold to Derive Structural Diversity and Functional Utility

Cyclic Dipeptide: A Privileged Molecular Scaffold to Derive Structural Diversity and Functional Utility

New Trends and Future Opportunities in the Enzymatic Formation of C−C, C−N, and C−O bonds

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

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