Pyrroloindole-Based Dynamic Combinatorial Chemistry

Gianga, Tiberiu-Marius; Rasadean, Dora-Maria; Pantoş, G. Dan

doi:10.3390/sym12050726

Cited by 3 publications

(6 citation statements)

References 61 publications

(83 reference statements)

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“…Therefore, 3,4dimethoxyphenyl was found to be the best substituent for azlactone in terms of high yield (86 %) and excellent diastereoand enantioselectivity (> 20 : 1 dr, 98 % ee). [53] Jian-Fei Bai et al have developed the first organocatalytic asymmetric formal [3 + 2] cycloaddition of 3-substituted 1Hindoles (73) with readily available propargylic alcohols (74) containing a functional directing group (p-NHAc or p-OH) in presence of chiral phosphoric acid or phosphoramides which yielded the title compounds (75) (Scheme 21). Authors conducted the reaction using various catalysts with different steric environments and backbones.…”

Section: Pyrrolo[12-a]indolesmentioning

confidence: 99%

“…Crystallographic analysis was used to determine the relative configuration of products. [73] Quan Cai et al have described acid catalyzed cascade Michael addition-cyclization of tryptamines. The reaction was initiated by treating readily available tryptamines (176) and enones (177) in presence of chiral phosphoric acid in toluene at rt for 8 h which afforded pyrroloindolines (178) (Scheme 42).…”

Section: Pyrroloindolinementioning

confidence: 99%

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Pyrroloindoles as Therapeutically Invaluable Agents: A Review on their Diverse Synthetic Methodologies

Ramesh,

Gattu,

Ramesh

2024

Asian J Org Chem

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In the realm of medicinal chemistry, heterocyclic compounds play a vital role due to their diverse pharmacological properties, especially, pyrroloindoles standing out as crucial motifs in drug development. Pyrroloindoles, which are formed by combining indole and pyrrole rings, exhibit unique characteristics and serve as integral components in numerous drugs and natural compounds. The synthesis of pyrroloindoles is challenging due to their complex ring structures and diverse substitution patterns. This comprehensive review compiles various synthetic strategies for obtaining pyrroloindole derivatives via metal‐catalyzed reactions; cyclopropanation/ ring opening/ iminium cyclization (CRI reaction); organocatalytic cascade addition‐cyclization; 1,3‐dipolar cycloaddition; Brønsted acid‐catalyzed [3+2] cyclodimerization; ring closure mechanisms; thermally‐induced ring‐opening and cyclization reactions; condensation reactions; and visible‐light photocatalytic asymmetric reactions providing a valuable resource for synthetic organic chemists and researchers interested in the synthesis of pyrroloindoles and their derivatives. These compounds play a pivotal role in drug discovery thus, making this review an indispensable reference.

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Section: Pyrrolo[12-a]indolesmentioning

confidence: 99%

Section: Pyrroloindolinementioning

confidence: 99%

Pyrroloindoles as Therapeutically Invaluable Agents: A Review on their Diverse Synthetic Methodologies

Ramesh,

Gattu,

Ramesh

2024

Asian J Org Chem

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“…In the skin and eyes of humans, kynurenine and its derivatives act as UV-A and VL absorbers, immunomodulators, and markers of oxidative distress. 315−319 The redox-active UV-A/HEVR-absorbing products of Trp oxidation, such as anthranilic acid, xanthurenic acid, melatonin, 5-methoxytryptamine and 5-methoxytryptophol, quinolinic acid, and picolinic acid, 315,320 play multiple roles in Table 3. continued metabolism and have been implicated in pathological conditions such as dementia.…”

Section: Amino Acidsmentioning

confidence: 99%

“…The kynurenine pathway is expressed at regulated levels in all skin cells and, in connection with the N -methyl- d -aspartate (NMDA) receptor, is responsible for cellular proliferation, differentiation, migration and, ultimately, skin barrier function. In the skin and eyes of humans, kynurenine and its derivatives act as UV-A and VL absorbers, immunomodulators, and markers of oxidative distress. − The redox-active UV-A/HEVR-absorbing products of Trp oxidation, such as anthranilic acid, xanthurenic acid, melatonin, 5-methoxytryptamine and 5-methoxytryptophol, quinolinic acid, and picolinic acid, , play multiple roles in metabolism and have been implicated in pathological conditions such as dementia . The Kyn pathway is required for the biosynthesis of NAD + , a central coenzyme in metabolism that is key for DNA repair under ionizing radiation …”

Section: Key Endogenous Photosensitizers and Their Targetsmentioning

confidence: 99%

Endogenous Photosensitizers in Human Skin

2023

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Endogenous photosensitizers play a critical role in both beneficial and harmful light-induced transformations in biological systems. Understanding their mode of action is essential for advancing fields such as photomedicine, photoredox catalysis, environmental science, and the development of sun care products. This review offers a comprehensive analysis of endogenous photosensitizers in human skin, investigating the connections between their electronic excitation and the subsequent activation or damage of organic biomolecules. We gather the physicochemical and photochemical properties of key endogenous photosensitizers and examine the relationships between their chemical reactivity, location within the skin, and the primary biochemical events following solar radiation exposure, along with their influence on skin physiology and pathology. An important take-home message of this review is that photosensitization allows visible light and UV-A radiation to have large effects on skin. The analysis presented here unveils potential causes for the continuous increase in global skin cancer cases and emphasizes the limitations of current sun protection approaches.

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“…Due to their ease of preparation and responsiveness to external triggers, dynamic combinatorial libraries (DCLs) based on this approach have found applications in a variety of fields, such as responsive systems and materials, [2–6] design of enzyme inhibitors, [7–11] cell recognition, [12] and self‐replicating molecules [13,14] . These applications are restricted to the dynamic bonds that are available, [15–22] each of them with limitations in terms of experimental conditions and functional group compatibility. As the applications of DCC grow, there is also an increasing demand for the discovery of new dynamic bonds to expand its scope [23] …”

Section: Introductionmentioning

confidence: 99%

Teaching an Old Compound New Tricks: Reversible Transamidation in Maleamic Acids

Matysiak

Santiago

Otto

2022

Chemistry A European J

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Dynamic combinatorial chemistry is a method widely used for generating responsive libraries of compounds, with applications ranging from chemical biology to materials science. It relies on dynamic covalent bonds that are able to form in a reversible manner in mild conditions, and therefore requires the discovery of new types of these bonds in order to progress. Amides, due to their high stability, have been scarcely used in this field and typically require an external catalyst or harsh conditions for exchange. Compounds able to undergo uncatalysed transamidation at room temperature are still rare exceptions. In this work, we describe reversible amide formation and transamidation in a class of compounds known as maleamic acids. Due to the presence of a carboxylic acid in β-position, these compounds are in equilibrium with their anhydride and amine precursors in organic solvents at room temperature. First, we show that this equilibrium is responsive to external stimuli: by alternating the additions of a Brønsted acid and a base, we can switch between amide and anhydride several times without side-reactions. Next, we prove that this equilibrium provides a pathway for reversible transamidation without any added catalyst, leading to thermodynamic distributions of amides at room temperature. Lastly, we use different preparation conditions and concentrations of Brønsted acid to access different library distributions, easily controlling the transition between kinetic and thermodynamic regimes. Our results show that maleamic acids can undergo transamidation in mild conditions in a reversible and tunable way, establishing them as a new addition to the toolbox of dynamic combinatorial chemistry.

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Pyrroloindole-Based Dynamic Combinatorial Chemistry

Cited by 3 publications

References 61 publications

Pyrroloindoles as Therapeutically Invaluable Agents: A Review on their Diverse Synthetic Methodologies

Pyrroloindoles as Therapeutically Invaluable Agents: A Review on their Diverse Synthetic Methodologies

Endogenous Photosensitizers in Human Skin

Teaching an Old Compound New Tricks: Reversible Transamidation in Maleamic Acids

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