Pub Date : 2026-01-30DOI: 10.1016/j.tetlet.2026.155982
Robert Junior Kolman , Nevena Milčić , Ivana Leščić Ašler , Zoran Štefanić , Petra Švaco , Višnja Stepanić , Zlatko Brkljača , Irena Dokli , Zvjezdana Findrik Blažević , Maja Majerić Elenkov
Halohydrin dehalogenases (HHDHs) offer a biocatalytic route to chiral azido alcohols and epoxides. In previous work, we reported an (R)-enantioselective azidolysis of fluorinated aromatic epoxides by HheC from Agrobacterium radiobacter AD1. Herein, we employed the HheA2-N178A variant, displaying high (S)-enantioselectivity, for the synthesis of a wide range of fluoroaromatic azido alcohols. Initially, we assayed 14 fluorinated styrene oxide derivatives and found high enantioselectivity in reactions (E up to 200), regardless of the substituent position. Biotransformations upscaled to 100 mM substrate concentration were carried out in a two-phase system, and the products were isolated in excellent enantiomeric purity (93 – >99% ee). Additionally, the structure of HheA2-N178A enzyme was determined.
{"title":"Biocatalytic synthesis of fluorine-containing chiral azido compounds in a two-phase system","authors":"Robert Junior Kolman , Nevena Milčić , Ivana Leščić Ašler , Zoran Štefanić , Petra Švaco , Višnja Stepanić , Zlatko Brkljača , Irena Dokli , Zvjezdana Findrik Blažević , Maja Majerić Elenkov","doi":"10.1016/j.tetlet.2026.155982","DOIUrl":"10.1016/j.tetlet.2026.155982","url":null,"abstract":"<div><div>Halohydrin dehalogenases (HHDHs) offer a biocatalytic route to chiral azido alcohols and epoxides. In previous work, we reported an (<em>R</em>)-enantioselective azidolysis of fluorinated aromatic epoxides by HheC from <em>Agrobacterium radiobacter</em> AD1. Herein, we employed the HheA2-N178A variant, displaying high (<em>S</em>)-enantioselectivity, for the synthesis of a wide range of fluoroaromatic azido alcohols. Initially, we assayed 14 fluorinated styrene oxide derivatives and found high enantioselectivity in reactions (<em>E</em> up to 200), regardless of the substituent position. Biotransformations upscaled to 100 mM substrate concentration were carried out in a two-phase system, and the products were isolated in excellent enantiomeric purity (93 – >99% <em>ee</em>). Additionally, the structure of HheA2-N178A enzyme was determined.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"178 ","pages":"Article 155982"},"PeriodicalIF":1.5,"publicationDate":"2026-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146096113","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-25DOI: 10.1016/j.tetlet.2026.155979
Qilong Lv, Yanchuan Zhao
CH functionalization has emerged as a powerful strategy in modern organic synthesis, enabling direct transformations of simple hydrocarbons into structurally diverse and value-added molecules. Among various approaches, diaryliodonium salts represent versatile intermediates that can be directly prepared from arenes and subsequently coupled with a wide range of nucleophiles, providing an efficient platform for rapid molecular diversification. However, one-step CH functionalization to access diaryliodonium salts often suffers from narrow substrate scope, while the ensuing coupling reactions are hampered by limitations in aryl transfer selectivity. These challenges have constrained the broader application of this methodology. Recent advances in the design of 3,5-dimethylisoxazol-4-yl (DMIX)-substituted hypervalent iodine reagents have simultaneously overcome both substrate and selectivity limitations, offering new opportunities for expanding the utility of diaryliodonium salts in CH functionalization. This review highlights the discovery and properties of DMIX-based reagents, and surveys their latest applications in achieving structurally diverse CH functionalization, highlighting their potential to advance the field of hypervalent iodine chemistry.
{"title":"Expanding the toolbox of CH functionalization: the emergence of DMIX-substituted hypervalent iodine reagents","authors":"Qilong Lv, Yanchuan Zhao","doi":"10.1016/j.tetlet.2026.155979","DOIUrl":"10.1016/j.tetlet.2026.155979","url":null,"abstract":"<div><div>C<img>H functionalization has emerged as a powerful strategy in modern organic synthesis, enabling direct transformations of simple hydrocarbons into structurally diverse and value-added molecules. Among various approaches, diaryliodonium salts represent versatile intermediates that can be directly prepared from arenes and subsequently coupled with a wide range of nucleophiles, providing an efficient platform for rapid molecular diversification. However, one-step C<img>H functionalization to access diaryliodonium salts often suffers from narrow substrate scope, while the ensuing coupling reactions are hampered by limitations in aryl transfer selectivity. These challenges have constrained the broader application of this methodology. Recent advances in the design of 3,5-dimethylisoxazol-4-yl (DMIX)-substituted hypervalent iodine reagents have simultaneously overcome both substrate and selectivity limitations, offering new opportunities for expanding the utility of diaryliodonium salts in C<img>H functionalization. This review highlights the discovery and properties of DMIX-based reagents, and surveys their latest applications in achieving structurally diverse C<img>H functionalization, highlighting their potential to advance the field of hypervalent iodine chemistry.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155979"},"PeriodicalIF":1.5,"publicationDate":"2026-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146075070","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-23DOI: 10.1016/j.tetlet.2026.155975
Melvin Raulin, Bruno Drouillat, Jérome Marrot, François Couty, Karen Wright
Prochiral 3-substituted azetidines bearing a chiral N-substituent may undergo ring-opening reactions with electrophiles, such as benzyl or propargyl bromide, to generate diastereomeric products with moderate selectivity. In the case of the resulting 3-bromo-N-propargylamines, reaction with sodium azide followed by intramolecular azide-alkyne cycloaddition led to substituted tetrahydro triazolodiazepine derivatives. These findings expand the utility of azetidine scaffolds for the construction of more complex nitrogen-containing heterocycles.
带有手性n取代基的前手性3-取代氮杂基可以与亲电试剂如苯或丙炔溴发生开环反应，生成具有中等选择性的非对映异构体产物。在得到3-溴- n -丙基胺的情况下，与叠氮化钠反应，然后在分子内叠氮化炔环加成，得到取代的四氢三氮杂氮衍生物。这些发现扩大了氮杂啶支架在构建更复杂的含氮杂环中的应用。
{"title":"Ring-opening of 3-substituted azetidines as an entry to triazolodiazepines","authors":"Melvin Raulin, Bruno Drouillat, Jérome Marrot, François Couty, Karen Wright","doi":"10.1016/j.tetlet.2026.155975","DOIUrl":"10.1016/j.tetlet.2026.155975","url":null,"abstract":"<div><div>Prochiral 3-substituted azetidines bearing a chiral <em>N</em>-substituent may undergo ring-opening reactions with electrophiles, such as benzyl or propargyl bromide, to generate diastereomeric products with moderate selectivity. In the case of the resulting 3-bromo-<em>N</em>-propargylamines, reaction with sodium azide followed by intramolecular azide-alkyne cycloaddition led to substituted tetrahydro triazolodiazepine derivatives. These findings expand the utility of azetidine scaffolds for the construction of more complex nitrogen-containing heterocycles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155975"},"PeriodicalIF":1.5,"publicationDate":"2026-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146025508","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-23DOI: 10.1016/j.tetlet.2026.155978
Amar Nath Singh Chauhan, Omkar S. Dalvi, Rohan D. Erande
Cannabinoids and indole–fused polycyclic natural products constitute a structurally diverse class of compounds possessing substantial pharmacological and industrial relevance. Multiple stereocenters, polycyclic frameworks, and sensitive functional groups pose persistent synthetic challenges, particularly for stereocontrolled access to their single enantiomers. Over the past two decades, promising synthetic pursuits, including Lewis acids catalyzed Friedel Crafts alkylation, chiral pool synthesis, terpene derivatization, biomimetic cyclizations, and Brønsted acid catalysis have enabled efficient as well as scalable synthetic routes to these complex scaffolds. These approaches not only allowed efficient synthesis of indole alkaloids such as murrayamines, hapalindoles, fischerindoles, and natural cannabinoids such as Δ9-THC, Δ8-THC, CBD, CBDV, CBDP, CBD-Hex, CBD-Oct, machaeriols, and epi-machaeriols, but also facilitated systematic exploration of stereochemistry for these natural products. By integrating synthetic protocols with structural–activity relationships, these strategies provided a versatile platform for designing next-generation analogues with tailored pharmacological profiles and industrial applications. This review highlights the recent advances (2005–2025) in Friedel–Crafts-driven synthetic strategies for efficiently constructing cannabinoids and indole–fused polycyclic scaffolds commenced from isopiperitenol, presenting the first unified compilation of targeted natural products derived from this versatile and readily accessible starting material. This comprehensive review emphasizes stereocontrolled, protecting-group-free, and scalable methods, including chiral pool synthesis, biomimetic cyclizations, and confined Brønsted acid catalysis, discussing synthetic pursuits and structure–activity relationships. Further, the review is systematically classified into five subsections 1] Introduction, 2] Aim and scope of review 3] Synthetic approaches 4] Conceptual framework and designing principles and 5] Conclusion.
{"title":"Recent advances in Friedel-Crafts reaction of isopiperitenol (2005–2025): concise way to synthesize bioinspired indole-fused polycycles and cannabinoids","authors":"Amar Nath Singh Chauhan, Omkar S. Dalvi, Rohan D. Erande","doi":"10.1016/j.tetlet.2026.155978","DOIUrl":"10.1016/j.tetlet.2026.155978","url":null,"abstract":"<div><div>Cannabinoids and indole–fused polycyclic natural products constitute a structurally diverse class of compounds possessing substantial pharmacological and industrial relevance. Multiple stereocenters, polycyclic frameworks, and sensitive functional groups pose persistent synthetic challenges, particularly for stereocontrolled access to their single enantiomers. Over the past two decades, promising synthetic pursuits, including Lewis acids catalyzed Friedel Crafts alkylation, chiral pool synthesis, terpene derivatization, biomimetic cyclizations, and Brønsted acid catalysis have enabled efficient as well as scalable synthetic routes to these complex scaffolds. These approaches not only allowed efficient synthesis of indole alkaloids such as murrayamines, hapalindoles, fischerindoles, and natural cannabinoids such as Δ<sup>9</sup>-THC, Δ<sup>8</sup>-THC, CBD, CBDV, CBDP, CBD-Hex, CBD-Oct, machaeriols, and <em>epi</em>-machaeriols, but also facilitated systematic exploration of stereochemistry for these natural products. By integrating synthetic protocols with structural–activity relationships, these strategies provided a versatile platform for designing next-generation analogues with tailored pharmacological profiles and industrial applications. This review highlights the recent advances (2005–2025) in Friedel–Crafts-driven synthetic strategies for efficiently constructing cannabinoids and indole–fused polycyclic scaffolds commenced from isopiperitenol, presenting the first unified compilation of targeted natural products derived from this versatile and readily accessible starting material. This comprehensive review emphasizes stereocontrolled, protecting-group-free, and scalable methods, including chiral pool synthesis, biomimetic cyclizations, and confined Brønsted acid catalysis, discussing synthetic pursuits and structure–activity relationships. Further, the review is systematically classified into five subsections 1] Introduction, 2] Aim and scope of review 3] Synthetic approaches 4] Conceptual framework and designing principles and 5] Conclusion.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155978"},"PeriodicalIF":1.5,"publicationDate":"2026-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146075073","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-22DOI: 10.1016/j.tetlet.2026.155981
Thalita O. Daher , Cristiane S. Schwalm , Sidnei Moura , Júlia Menin , Bárbara Tirloni , Gleison A. Casagrande , Lucas Pizzuti
A practical and metal-free approach to 1-thiazolyl-1H-indazoles was developed starting from readily available o-fluorobenzaldehydes. The method involves initial condensation with thiosemicarbazide and 2-bromoacetophenone to form o-fluorobenzaldehyde thiazolylhydrazones, followed by base-promoted intramolecular cyclization through nucleophilic aromatic substitution. After optimization of conditions, the reaction showed broad functional group tolerance and clear substituent effects, with halogens (Br, Cl) outperforming additional F or NO₂ due to cleaner conversions and easier isolation. The transformation proved scalable; a gram-scale experiment confirmed its practicality and enabled subsequent CBr functionalization of the indazole core, further underscoring the synthetic utility of this approach. Structural assignments were confirmed by HRMS, 1H and 13C NMR, and single-crystal X-ray diffraction.
{"title":"Synthesis of 1-thiazolyl-1H-indazoles from o-fluorobenzaldehyde thiazolylhydrazones","authors":"Thalita O. Daher , Cristiane S. Schwalm , Sidnei Moura , Júlia Menin , Bárbara Tirloni , Gleison A. Casagrande , Lucas Pizzuti","doi":"10.1016/j.tetlet.2026.155981","DOIUrl":"10.1016/j.tetlet.2026.155981","url":null,"abstract":"<div><div>A practical and metal-free approach to 1-thiazolyl-1<em>H</em>-indazoles was developed starting from readily available <em>o</em>-fluorobenzaldehydes. The method involves initial condensation with thiosemicarbazide and 2-bromoacetophenone to form <em>o</em>-fluorobenzaldehyde thiazolylhydrazones, followed by base-promoted intramolecular cyclization through nucleophilic aromatic substitution. After optimization of conditions, the reaction showed broad functional group tolerance and clear substituent effects, with halogens (Br, Cl) outperforming additional F or NO₂ due to cleaner conversions and easier isolation. The transformation proved scalable; a gram-scale experiment confirmed its practicality and enabled subsequent C<img>Br functionalization of the indazole core, further underscoring the synthetic utility of this approach. Structural assignments were confirmed by HRMS, <sup>1</sup>H and <sup>13</sup>C NMR, and single-crystal X-ray diffraction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155981"},"PeriodicalIF":1.5,"publicationDate":"2026-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146075072","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-22DOI: 10.1016/j.tetlet.2026.155980
Jin Jiang , Zhuo Wang , Lili Xiao
A method for the debenzylation of benzyl esters has been developed, utilizing easy-to-operate diiodine and triethylsilane. This procedure can be carried out in an air atmosphere at room temperature, without the need for transition metals or hydrogen. Halogen, hydroxyl, methoxy, ester, nitro and other functional groups are compatible with this debenzylation.
{"title":"Cleavage of benzyl esters by diiodine–triethylsilane system","authors":"Jin Jiang , Zhuo Wang , Lili Xiao","doi":"10.1016/j.tetlet.2026.155980","DOIUrl":"10.1016/j.tetlet.2026.155980","url":null,"abstract":"<div><div>A method for the debenzylation of benzyl esters has been developed, utilizing easy-to-operate diiodine and triethylsilane. This procedure can be carried out in an air atmosphere at room temperature, without the need for transition metals or hydrogen. Halogen, hydroxyl, methoxy, ester, nitro and other functional groups are compatible with this debenzylation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155980"},"PeriodicalIF":1.5,"publicationDate":"2026-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146075125","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-21DOI: 10.1016/j.tetlet.2026.155977
Wei Liu , Xiaoning Yang , Jiayi Wang , Gonghua Song
A novel, environmentally friendly and highly efficient protocol has been developed for the synthesis of unsymmetrical disulfides via a photochemical radical cross-coupling reaction between sulfenyl chlorides and thiols under LED irradiation. The process does not need any catalyst or additive. The high-yield recovery of the solvent and the primary by-product makes this method highly atom-economical.
{"title":"Photochemical cross-coupling between sulfenyl chlorides and thiols: a facile, catalyst- and additive-free access to unsymmetrical disulfides","authors":"Wei Liu , Xiaoning Yang , Jiayi Wang , Gonghua Song","doi":"10.1016/j.tetlet.2026.155977","DOIUrl":"10.1016/j.tetlet.2026.155977","url":null,"abstract":"<div><div>A novel, environmentally friendly and highly efficient protocol has been developed for the synthesis of unsymmetrical disulfides <em>via</em> a photochemical radical cross-coupling reaction between sulfenyl chlorides and thiols under LED irradiation. The process does not need any catalyst or additive. The high-yield recovery of the solvent and the primary by-product makes this method highly atom-economical.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155977"},"PeriodicalIF":1.5,"publicationDate":"2026-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146075071","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-20DOI: 10.1016/j.tetlet.2026.155976
Jesscia E. Carsley, Mason T. Gates, Kimberly S. Petersen
Microwave reactors have been used in organic synthesis to facilitate reactions since the 1980s. In this paper we show that the reaction time can be substantially shortened for our previously developed chiral Brønsted acid catalyzed desymmetrization of diesters to yield lactones when performed in the microwave from 72 h to 20 min without loss in yield or enantiopurity. Three additional organocatalyzed asymmetric reactions from current literature were explored and shown to exhibit similar benefits with the use of a microwave reactor. Although not traditionally thought of as a tool in asymmetric organocatalysis, we show that microwave reactors can benefit many enantioselective reactions, particularly those with long reaction times.
{"title":"Microwave reactor assisted chiral Brønsted acid catalyzed asymmetric synthesis","authors":"Jesscia E. Carsley, Mason T. Gates, Kimberly S. Petersen","doi":"10.1016/j.tetlet.2026.155976","DOIUrl":"10.1016/j.tetlet.2026.155976","url":null,"abstract":"<div><div>Microwave reactors have been used in organic synthesis to facilitate reactions since the 1980s. In this paper we show that the reaction time can be substantially shortened for our previously developed chiral Brønsted acid catalyzed desymmetrization of diesters to yield lactones when performed in the microwave from 72 h to 20 min without loss in yield or enantiopurity. Three additional organocatalyzed asymmetric reactions from current literature were explored and shown to exhibit similar benefits with the use of a microwave reactor. Although not traditionally thought of as a tool in asymmetric organocatalysis, we show that microwave reactors can benefit many enantioselective reactions, particularly those with long reaction times.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155976"},"PeriodicalIF":1.5,"publicationDate":"2026-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146025507","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
An efficient quinazoline-assisted ortho-acetoxylation of 4-phenylquinazoline has been developed using PhI(OAc)2 as both the oxidizing agent and acetoxy source under Pd(II)-catalyzed CH activation. The protocol exhibits high regioselectivity and functional group tolerance with yields up to 98%. Radical scavenging experiments indicate that the acetoxylation involves an acetoxy radical pathway.
{"title":"Palladium-catalyzed regioselectivity CH acetoxylation of 4-phenylquinazoline","authors":"Mushou Cai, Tongtong Deng, Shifeng Xin, Hongjun Zhu","doi":"10.1016/j.tetlet.2026.155974","DOIUrl":"10.1016/j.tetlet.2026.155974","url":null,"abstract":"<div><div>An efficient quinazoline-assisted <em>ortho-</em>acetoxylation of 4-phenylquinazoline has been developed using PhI(OAc)<sub>2</sub> as both the oxidizing agent and acetoxy source under Pd(II)-catalyzed C<img>H activation. The protocol exhibits high regioselectivity and functional group tolerance with yields up to 98%. Radical scavenging experiments indicate that the acetoxylation involves an acetoxy radical pathway.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155974"},"PeriodicalIF":1.5,"publicationDate":"2026-01-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146025488","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-19DOI: 10.1016/j.tetlet.2026.155972
Xiao-Yu Qi , Yu-Zhou Fan , An-Yu Li , Xue-Fei Li , Jia-Mei Tang , Yuan-Liang Xu , Yan Liu , Xue-Mei Niu , Kai Guo , Sheng-Hong Li
Gentianellin A (1), a new gentianellane-type sesterterpenoid possessing a 5/7/5/6/5 pentacyclic ring system formed by a bridged ether bond, was isolated from the traditional Tibetan medicine Gentianella azurea. Its structure was elucidated by extensive spectroscopic analysis, single-crystal X-ray diffraction, and quantum chemical calculations. Compound 1 exhibited immunosuppressive activity by inhibiting the secretion of IL-6 and TNF-α in LPS-induced macrophages RAW264.7 with IC50 values of 13.80 and 18.46 μM.
{"title":"Gentianellin A, an unusual immunosuppressive sesterterpenoid from the traditional Tibetan medicine Gentianella azurea","authors":"Xiao-Yu Qi , Yu-Zhou Fan , An-Yu Li , Xue-Fei Li , Jia-Mei Tang , Yuan-Liang Xu , Yan Liu , Xue-Mei Niu , Kai Guo , Sheng-Hong Li","doi":"10.1016/j.tetlet.2026.155972","DOIUrl":"10.1016/j.tetlet.2026.155972","url":null,"abstract":"<div><div>Gentianellin A (<strong>1</strong>), a new gentianellane-type sesterterpenoid possessing a 5/7/5/6/5 pentacyclic ring system formed by a bridged ether bond, was isolated from the traditional Tibetan medicine <em>Gentianella azurea</em>. Its structure was elucidated by extensive spectroscopic analysis, single-crystal X-ray diffraction, and quantum chemical calculations. Compound <strong>1</strong> exhibited immunosuppressive activity by inhibiting the secretion of IL-6 and TNF-α in LPS-induced macrophages RAW264.7 with IC<sub>50</sub> values of 13.80 and 18.46 μM.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155972"},"PeriodicalIF":1.5,"publicationDate":"2026-01-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145993575","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
扫码关注我们
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号