Article
Chemistry, Inorganic & Nuclear
Xiuru Bi, Luyao Tao, Nan Yao, Mingxia Gou, Gexin Chen, Xu Meng, Peiqing Zhao
Summary: In this study, a H3PO4 center dot 12WO(3)/OMS-2 nanocomposite catalyst was successfully prepared, leading to the synthesis of β-carbolines and 3,4-dihydro-β-carbolines by tuning reaction conditions. The catalyst exhibited excellent activity, high selectivity, and good stability, providing a practical pathway for flexible and controllable synthesis of novel compounds.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Maneesh Mohan, Susan P. P. Eldhose, Athul Sudheendranath, E. G. Jayasree, Ani Deepthi
Summary: A green stereoselective synthesis of spiroheterocycles incorporating a spirooxindole and a 1,2,3,4-tetrahydro-beta-carboline (TH beta C) is demonstrated. The reaction is simple, chromatography-free, and yields densely substituted spiroheterocycles with excellent yields. In silico studies show that the compounds exhibit excellent binding interactions with MDM2 and PLK1 target proteins compared to reference drugs.
SYNTHESIS-STUTTGART
(2023)
Article
Oncology
Xiaoyan Xing, Fahui Li, Yajie Hu, Lin Zhang, Qian Hui, Hongyu Qin, Qixiao Jiang, Wenyan Jiang, Chunyan Fang, Lei Zhang
Summary: This study identified potent APN inhibitors that could be used as lead compounds for tumor chemo-sensitization and cancer stem cell-based therapies.
FRONTIERS IN ONCOLOGY
(2022)
Article
Chemistry, Physical
Zhenguo Zhang, Xiaoxiao Liu, Liang Ji, Ting Zhang, Zhenhua Jia, Teck-Peng Loh
Summary: This study reveals the synthesis of diverse tetrahydro-beta-carbolines and spirocyclic tetrahydro-beta-carbolines through the unprecedented triarylcarbonium ion-pair-catalyzed reaction in water under metal-free conditions. The reaction shows good yields and excellent functional group tolerance, allowing for late-stage modification of natural products and small molecular drugs.
Article
Chemistry, Physical
Jinmei Zhu, Lu Yang, Jiequn Wu, Zixin Deng, Xudong Qu
Summary: By improving the specificity synthesis method for sterically hindered amines, researchers successfully synthesized the important 1-aryl-tetrahydro-beta-carboline framework, providing a new approach for its application in natural products and pharmaceuticals.
Article
Chemistry, Multidisciplinary
Rina Mahato, Chinmoy Kumar Hazra
Summary: In this study, pentafluorophenol was revealed as an effective catalyst for the synthesis of (spirocyclic) tetrahydro-beta-carbolines via the Pictet-Spengler reaction. This straightforward catalytic system operates under mild conditions, yielding indole alkaloids in excellent yield and exhibiting remarkable functional group tolerance, including late-stage modifications. This transformation provides a practical and adaptable approach for the gram-scale synthesis of the natural alkaloid Komavine and enables the synthesis of the commercial drug Tadalafil.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Yogesh Brijwashi Sharma, Rajveer Singh, Chetan Paul Singh, Yogesh P. Bharitkar, Abhijit Hazra
Summary: In this study, a one-step synthesis of tetrahydro-beta-carbolino-spiroindolone/spiroacenapthylene scaffold from tryptamine and isatin was achieved using lemon juice as a biocatalyst system via Pictet-Spengler Reaction. The reaction provided clean and convenient synthesis of spiroindolones. The product was separated and characterized using chromatographic and spectroscopic techniques. Bio evaluation showed promising activity against several cancer cell lines for specific compounds.
Article
Chemistry, Organic
Arka Das, Christine Jonathan, Rana Saha, Md Imran Ahmed, Subhendu Bhowmik
Summary: A regioselective decarboxylative alkynylation of tetrahydro-beta-carboline-1-carboxylic acid under peroxide-free condition is reported, which exhibits high selectivity for the 1-position of tetrahydro-beta-carboline. Depending on the reagent, the reaction can produce alkynylated or enaminone products. The reaction proceeds through sequential decarboxylative iminium ion formation followed by an alkynylation and oxidative rearrangement cascade.
Article
Chemistry, Physical
Shubham Lata, Sourav Taru Saha, Mandeep Kaur, Paul Awolade, Oluwakemi Ebenezer, Parvesh Singh, Vipan Kumar, Vipan Kumar
Summary: This study designed and synthesized a series of tetrahydro-beta-carboline-naphthalimide hybrids. Through evaluating their growth inhibitory potential against breast cancer cell lines and studying their interactions with estrogen receptor, the success rate and potential of hybridization technique in cancer treatment were demonstrated.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Biochemistry & Molecular Biology
Vipin Kumar, Anjali Saxena, Ranjan Patra, Devalina Ray, Hong-yu Li, Biswajit Saha
Summary: Ugi-four component reaction (Ugi-4CR) is an attractive method for diversity-oriented and step economical synthesis, as shown by its past applications. In this study, we report a method for the synthesis of fused polycyclic beta-carboline derivatives through sequential Pictet-Spengler's and Ugi-4CR multi-component reactions followed by cascade cyclization. The resulting conformationally stable heterocyclic molecules are expected to have potential interactions with different biological targets. This methodology provides a simple and facile access to heterocycles embedded in polycyclic frameworks that are difficult to synthesize using conventional methods.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Physical
Khaled M. Darwish, Ahmad Abdelwaly, Asmaa M. Atta, Mohamed A. Helal
Summary: The synthesized compounds showed potential in inhibiting PDE4 and exhibited good selectivity and specific interactions at the PDE4 active site.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Organic
Linsong Yang, Jianjiong Li, Zefei Xu, Peiyuan Yao, Qiaqing Wu, Dunming Zhu, Yanhe Ma
Summary: In this study, an efficient and environmentally friendly enzymatic approach was developed to synthesize optically pure chiral fused-ring THIQs and TH β Cs with high enantioselectivity and conversion.
Article
Chemistry, Medicinal
Veena D. Yadav, Lalan Kumar, Poonam Kumari, Sakesh Kumar, Maninder Singh, Mohammad I. Siddiqi, Prem N. Yadav, Sanjay Batra
Summary: The synthesis of new fused beta-carboline derivatives led to the discovery of two compounds with significant agonistic activity on KOR, which were found to be extremely G-protein-biased agonists. These compounds demonstrated analgesic effects in mice, without inducing sedation, and their interaction with the human KOR was studied for rationalization of the results.
Article
Chemistry, Organic
Jay Prakash Soni, Manda Sathish, Fabiane M. Nachtigall, Leonardo S. Santos, Nagula Shankaraiah
Summary: The Pictet-Spengler reaction is an efficient synthetic tool for constructing tetrahydro-beta-carbolines and tetrahydroisoquinolines, with a brown seaweed-derived alginic acid reported as an effective reusable catalyst. The protocol shows good yields with various aliphatic and aromatic aldehydes, and demonstrates sustainable synthesis of different compounds including a natural spirooxindole. The catalyst was found to be reusable with no significant deterioration in reaction yields observed up to the 6th cycle.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Somnath S. Gholap, Vinod R. Kadu
Summary: The synthesis of structurally diversified beta-carboline derivatives using a readily available natural surfactant medium has been reported. The reaction of tryptamine with aldehydes in an aqueous extract of Acacia Concinna pods yielded good results, suggesting potential for cost-effective large-scale production of beta-carboline derivatives.
RESULTS IN CHEMISTRY
(2021)
