Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group

Lassalas, Pierrik; Oukoloff, Killian; Makani, Vishruti; James, Michael J.; Tran, Van Tan; Yao, Yuemang; Huang, Li-Hsin; Vijayendran, Krishna G.; Monti, Ludovica; Trojanowski, John Q.; Lee, Virginia M.‐Y.; Kozlowski, Marisa C.; Smith, Amos B.; Brunden, Kurt R.; Ballatore, Carlo

doi:10.1021/acsmedchemlett.7b00212

Cited by 36 publications

(30 citation statements)

References 29 publications

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“…Oxetanes can act as suitable polar replacement groups for gem ‐dimethyl linkers and as bioisosteres for carbonyl functionality . In recent years, oxetane isosteres have been presented for amide, ketone and carboxylic acid derivatives . These developments continue to accelerate the exploration of oxetanes in medicinal chemistry …”

Section: Figurementioning

confidence: 99%

Lithium‐Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3‐Sulfanyl‐Oxetanes as Bioisosteres

Croft

Mousseau

Choi

et al. 2017

Chemistry A European J

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Abstract3‐Sulfanyl‐oxetanes are presented as promising novel bioisosteric replacements for thioesters or benzyl sulfides. From oxetan‐3‐ols, a mild and inexpensive Li catalyst enables chemoselective C−OH activation and thiol alkylation. Oxetane sulfides are formed from various thiols providing novel motifs in new chemical space and specifically as bioisosteres for thioesters due to their similar shape and electronic properties. Under the same conditions, various π‐activated secondary and tertiary alcohols are also successful. Derivatization of the oxetane sulfide linker provides further novel oxetane classes and building blocks. Comparisons of key physicochemical properties of the oxetane compounds to selected carbonyl and methylene analogues indicate that these motifs are suitable for incorporation into drug discovery efforts.

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Section: Figurementioning

confidence: 99%

Lithium‐Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3‐Sulfanyl‐Oxetanes as Bioisosteres

Croft

Mousseau

Choi

et al. 2017

Chemistry A European J

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“…Bioisosterism denote that two different molecules can afford similar biological responses if the structural features are accomplished by physicochemical property that is responsible in great measure of the biological response. This concept was coined by Friedman [ 39 ], extended by Burger [ 40 ] and recently used by Lassalas et al [ 41 ] and Tahirova [ 42 ].…”

Section: Resultsmentioning

confidence: 99%

Maximum common property: a new approach for molecular similarity

et al. 2020

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The maximum common property similarity (MCPhd) method is presented using descriptors as a new approach to determine the similarity between two chemical compounds or molecular graphs. This method uses the concept of maximum common property arising from the concept of maximum common substructure and is based on the electrotopographic state index for atoms. A new algorithm to quantify the similarity values of chemical structures based on the presented maximum common property concept is also developed in this paper. To verify the validity of this approach, the similarity of a sample of compounds with antimalarial activity is calculated and compared with the results obtained by four different similarity methods: the small molecule subgraph detector (SMSD), molecular fingerprint based (OBabel_FP2), ISIDA descriptors and shape-feature similarity (SHAFTS). The results obtained by the MCPhd method differ significantly from those obtained by the compared methods, improving the quantification of the similarity. A major advantage of the proposed method is that it helps to understand the analogy or proximity between physicochemical properties of the molecular fragments or subgraphs compared with the biological response or biological activity. In this new approach, more than one property can be potentially used. The method can be considered a hybrid procedure because it combines descriptor and the fragment approaches.

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“…Bioisosterism means that two different molecules can provide similar biological responses if the structural aspects are phenomenologically accompanied by a physicochemical property associated with the biological response. This concept was coined by Friedman [26], extended by Burger [27] and recently used by Lassalas et al [28] and Tahirova [29].…”

Section: Resultsmentioning

confidence: 99%

Maximum Common Property: A New Approach for Molecular Similarity

García

Collado

Carrasco-Velar

et al. 2020

Preprint

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The maximum common property similarity (MCPhd) method is presented using descriptors as a new approach to determine the similarity between two chemical compounds or molecular graphs. This method uses the concept of maximum common property arising from the concept of maximum common substructure and is based on the electrotopographic state index for atoms. A new algorithm to quantify the similarity values of chemical structures based on the presented maximum common property concept is also developed in this paper. To verify the validity of this approach, the similarity of a sample of compounds with antimalarial activity is calculated and compared with the results obtained by the small molecule subgraph detector (SMSD) method. The results obtained by the MCPhd method differ significantly from those obtained by the SMSD method, improving the quantification of the similarity. A major advantage of the proposed method is that it helps to understand the analogy or proximity between physicochemical properties of the molecular fragments or subgraphs compared with the biological response or biological activity. In this new approach, more than one property can be potentially used. The method can be considered a hybrid procedure because it combines descriptor and the fragment approaches.

show abstract

Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group

Cited by 36 publications

References 29 publications

Lithium‐Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3‐Sulfanyl‐Oxetanes as Bioisosteres

Lithium‐Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3‐Sulfanyl‐Oxetanes as Bioisosteres

Maximum common property: a new approach for molecular similarity

Maximum Common Property: A New Approach for Molecular Similarity

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