Recent ring distortion reactions for diversifying complex natural products

Liu, Yu; Cheng, Shihao; Tian, Ye; Zhang, Yanan; Zhao, Yu

doi:10.1039/d2np00027j

Cited by 14 publications

(5 citation statements)

References 89 publications

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“…Nevertheless, the future development of NIMO still comes up against a few open questions. NIMO can mimic fragment rearrangement, ring separation, and ring combination (edge fusion), but some other more complicated design strategies, such as opening/closing ring and bridged ring, were not realized to generate pseudo-NPs in the current work [11,50,51].…”

Section: Discussionmentioning

confidence: 99%

NIMO: A Natural Product-Inspired Molecular Generative Model Based on Conditional Transformer

Shen,

Zeng,

Chen

et al. 2024

Molecules

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Natural products (NPs) have diverse biological activity and significant medicinal value. The structural diversity of NPs is the mainstay of drug discovery. Expanding the chemical space of NPs is an urgent need. Inspired by the concept of fragment-assembled pseudo-natural products, we developed a computational tool called NIMO, which is based on the transformer neural network model. NIMO employs two tailor-made motif extraction methods to map a molecular graph into a semantic motif sequence. All these generated motif sequences are used to train our molecular generative models. Various NIMO models were trained under different task scenarios by recognizing syntactic patterns and structure–property relationships. We further explored the performance of NIMO in structure-guided, activity-oriented, and pocket-based molecule generation tasks. Our results show that NIMO had excellent performance for molecule generation from scratch and structure optimization from a scaffold.

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Section: Discussionmentioning

confidence: 99%

NIMO: A Natural Product-Inspired Molecular Generative Model Based on Conditional Transformer

Shen,

Zeng,

Chen

et al. 2024

Molecules

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“…Rearrangement reactions play a critical role in constructing novel skeletons of natural products, [58][59][60] with a carbocation oen a vital intermediate in this process. 61,62 The possible biosynthetic pathway of ganodermaone A (104) 63 from G. cochlear is taken as an example of a possible carbocation-related rearrangement reaction.…”

Section: Type V Gms (Rearranged Side Chain)mentioning

confidence: 99%

Structural diversity, hypothetical biosynthesis, chemical synthesis, and biological activity ofGanodermameroterpenoids

et al. 2023

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“…Complexity-to-diversity strategies use available NPs as starting points, which are then subjected to different chemical transformations resulting in new derivative compound classes with different ring structures and bioactivity. [20] In general, CtD involves the modification of complex ring systems through a few reactions step, facilitating ring cleavage, rearrangement, expansion, and fusion. This approach has been successfully applied with ketone-and alkene-reactivity, together with molecular frameworks capable of inducing dramatic ring distortion reactions.…”

Section: Photo-reactivity Of αβ-Unsaturated Carbonyl Group From Solid...mentioning

confidence: 99%

Expanding Diterpene Complexity and Diversity via Photoinduced Ring Distortions

Luz Tibaldi‐Bollati,

Nicotra,

Oksdath‐Mansilla

et al. 2023

ChemPlusChem

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Natural products and their semi‐synthetic derivatives undoubtedly constitute an important source of therapeutic agents. Their importance lies in their own origin and evolution, since they have great chemical diversity, biochemical specificity, and pharmacological properties. Currently, there is a renewed interest in the development of methodologies capable of efficiently modifying the chemical structure of these bioactive platforms. In this work, the photoderivatization of the diterpene solidagenone was performed using a complexity‐to‐diversity‐oriented approach. By exploring [2+2]‐photocycloaddition, photoinduced‐hydrogen abstraction, and photoxygenation reactions, a set of solidagenone derivatives was obtained, showing different ring fusions, side chain rearrangements, and modifications of the original furan ring's substitution pattern. The derivatives obtained were characterised by NMR methodologies. To evaluate the structural diversity of the labdane‐derived compounds, their physicochemical properties, structural similarity, and chemical space were analysed. These results suggest that photochemical reactions are a useful tool for performing ring distortion transformations, generating derivatives of natural compounds with wide diversity, structural complexity, and with potential biological properties.

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Recent ring distortion reactions for diversifying complex natural products

Abstract: The ring distortion reactions recently used in complexity-to-diversity and pseudo natural product strategies for diversifying complex natural products have been overviewed.

Cited by 14 publications

References 89 publications

NIMO: A Natural Product-Inspired Molecular Generative Model Based on Conditional Transformer

NIMO: A Natural Product-Inspired Molecular Generative Model Based on Conditional Transformer

Structural diversity, hypothetical biosynthesis, chemical synthesis, and biological activity ofGanodermameroterpenoids

Expanding Diterpene Complexity and Diversity via Photoinduced Ring Distortions

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