Synthetic pathways to create asymmetric center at C1 position of 1-substituted-tetrahydro-β-carbolines – a review DOI Creative Commons
Md. Moaz Ahmed Asif,

Susmita Roy Lisa,

Nazmul Qais

и другие.

RSC Advances, Год журнала: 2024, Номер 14(41), С. 29827 - 29847

Опубликована: Янв. 1, 2024

Chiral 1-substituted-THβC can be synthesized from l -tryptophan or tryptamine by Pictet–Spengler reaction and chiral auxiliary; also substituted-DHβC ATH with catalysts, asymmetric addition reaction, enzymatic catalysis.

Язык: Английский

Recent advances on electrochemical generation of sulfonyl radical triggered cyclization of alkene/alkynes DOI

Jiaqing Shao,

Jiang Liu, Haibo Mei

и другие.

Tetrahedron, Год журнала: 2025, Номер 173, С. 134467 - 134467

Опубликована: Янв. 12, 2025

Язык: Английский

Процитировано

3
FDA‐approved drugs featuring macrocycles or medium‐sized rings DOI Creative Commons

Youlong Du,

Anas Semghouli,

Qian Wang

и другие.

Archiv der Pharmazie, Год журнала: 2025, Номер 358(1)

Опубликована: Янв. 1, 2025

Abstract Macrocycles or medium‐sized rings offer diverse functionality and stereochemical complexity in a well‐organized ring structure, allowing them to fulfill various biochemical functions, resulting high affinity selectivity for protein targets, while preserving sufficient bioavailability reach intracellular compartments. These features have made macrocycles attractive candidates organic synthesis drug discovery. Since the 20th century, more than three‐score macrocyclic drugs, including radiopharmaceuticals, been approved by US Food Drug Administration (FDA) treating bacterial viral infections, cancer, obesity, immunosuppression, inflammatory, neurological disorders, managing cardiovascular diseases, diabetes, more. This review presents 17 FDA‐approved drugs during past 5 years, highlighting their importance critical role modern therapeutics, innovative synthetic approaches construction of these macrocycles.

Язык: Английский

Процитировано

2
Synthesis of 1‐Aryl‐β‐Carbolines via a Pd‐Catalyzed Oxidative Pictet‐Spengler Reaction/Aromatization Cascade Using Benzylic Alcohols in Water DOI Open Access
Masakazu Kobayashi, Hidemasa Hikawa,

Tomokatsu Enda

и другие.

European Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 3, 2025

Abstract We report a Pd‐catalyzed oxidative Pictet‐Spengler reaction/aromatization cascade utilizing readily available benzylic alcohols for the construction of 1‐aryl‐ β ‐carbolines in water. Conceptually, this novel one‐pot, three‐step approach involves an initial Pd(0)/sodium diphenylphosphinobenzene‐3‐sulfonate (TPPMS)‐catalyzed dehydrogenation alcohols, followed by cyclization situ generated aldehydes with tryptamines, and concludes DBU/air‐promoted aromatization, allowing rapid access to desired ‐carbolines. The π ‐benzylPd (II) catalytic system from Pd(0)/TPPMS was found be highly effective alcohol

Язык: Английский

Процитировано

1
Rapid Synthesis of 3,7a-Diazacyclohepta[jk]fluorenes via Cascade Michael Addition/Pictet–Spengler Reaction and Amidation Reaction DOI
B. J. Wei, Yanlong Gong, Xue Meng

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

In this article, a convenient method has been developed for the rapid and expedient diastereoselective synthesis of highly functionalized 3,7a-diazacyclohepta[jk]fluorenes from simple starting materials via cascade Michael addition/Pictet-Spengler reaction amidation reaction. addition, whole process, losing only one molecule water alcohol, high atomic economy.

Язык: Английский

Процитировано

0
Dipolar Cycloaddition Approach toward Harmicine-Type Alkaloids: Synthesis and Stereochemical Determination DOI

Zuming Lin,

Luyao Wu,

Shengchao Yang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 31, 2025

A rapid synthesis of harmicine was achieved through 1,3-dipolar cycloaddition and facile ring reconstruction, including mesylation, cleavage the N-O bond, subsequent cyclization. An enzymatic kinetic resolution developed to obtain optically enriched tetrahydro-β-carboline, which further elaborated prepare harmicine. Additionally, diastereomeric harmicinic acid also achieved, stereochemical determination enabled by chemical electronic circular dichroism calculations for first time, providing an intriguing platform access various derivatives future medicinal research.

Язык: Английский

Процитировано

0
Electrochemical synthesis of γ-carbolinones via sulfonylation-triggered cyclization of indole-3-carboxamides DOI
Dan Luo, Qian Wang, Jiang Liu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 5, 2024

A novel electrochemical cyclization reaction of N -acryloyl-indole-3-carboxamides has been developed, which provides a new and efficient strategy for the synthesis γ-carbolinone derivatives.

Язык: Английский

Процитировано

2
Synthetic pathways to create asymmetric center at C1 position of 1-substituted-tetrahydro-β-carbolines – a review DOI Creative Commons
Md. Moaz Ahmed Asif,

Susmita Roy Lisa,

Nazmul Qais

и другие.

RSC Advances, Год журнала: 2024, Номер 14(41), С. 29827 - 29847

Опубликована: Янв. 1, 2024

Chiral 1-substituted-THβC can be synthesized from l -tryptophan or tryptamine by Pictet–Spengler reaction and chiral auxiliary; also substituted-DHβC ATH with catalysts, asymmetric addition reaction, enzymatic catalysis.

Язык: Английский

Процитировано

1