69954-48-9Relevant academic research and scientific papers
Unusual formation of β-carboline dimers under Bischler-Napieralski reaction conditions: An old reaction with a new direction
Pal, Bikash,Jaisankar, Parasuraman,Sesha Giri, Venkatachalam,Mondal, Swastik,Mukherjee, Monika
, p. 6489 - 6492 (2004)
L-N-Formyl tryptophan methyl ester (3) underwent a Bischler-Napieralski reaction with POCl3 at room temperature or under microwave irradiation, resulting in the unusual formation of -carboline dimers 5 and 6. Most importantly, acetylation using Ac2O of each of the dimers 5 and 6 separately afforded 1-[3′-carbomethoxy-β-carbolinyl]-3- carbomethoxy-9-acetyl-β-carboline (7) as the only product, the structure of which was confirmed by X-ray crystallography studies.
Structure-Based Design and Synthesis of N-Substituted 3-Amino-β-Carboline Derivatives as Potent αβ-Tubulin Degradation Agents
Bai, Peng,Chen, Lijuan,Fu, Suhong,Han, Kai,He, Wen,Li, Jiewen,Li, Yong,Liu, Jiang,Liu, Yan,Shi, Mingsong,Tang, Minghai,Xie, Lixin,Yan, Wei,Yang, Jianhong,Yang, Zhuang,Ye, Haoyu,Zhang, Chufeng,Zhu, Zejiang
, p. 2675 - 2693 (2022/02/10)
So far, relatively few small molecules have been reported to promote tubulin degradation. Our previous studies have found that compound 2, a noncovalent colchicine-site ligand, was capable of promoting αβ-tubulin degradation. To further improve its antipr
Discovery of β-carboline-(phenylsulfonyl)furoxan hybrids as potential anti-breast cancer agents
Hu, Xu,Gao, Xiang,Gao, Gang,Wang, Yanbing,Cao, Hao,Li, Dahong,Hua, Huiming
supporting information, (2021/04/02)
The cytotoxicity properties of the β-carboline alkaloids have been broadly investigated. However, the potential application of β-carbolines was hindered due to the moderate activity in cancer. In the present study, thirty β-carboline-(phenylsulfonyl)furoxan hybrids (11a–j, 12a–j and 13a–j) were designed and synthesized through esterification and amidation reaction strategy, and their inhibitory activities against the human breast cancer cell lines MCF-7 and MDA-MB-231 were evaluated by CCK-8 assay. Biological evaluation presented that the most promising amide derivative 13h, substituted with p-methoxyphenyl group at position 1, generated high concentration of NO and evidently depressed the MCF-7 (IC50 = 0.89 μM) and MDA-MB-231 (IC50 = 0.62 μM) cells proliferation. Particularly, the wound healing and transwell assays demonstrated that 13h significantly inhibited the migration and invasion of MDA-MB-231cells. Furthermore, the preliminary mechanisms studies indicated that 13h induced G2/M phase arrest and apoptosis possibly causing by ROS accumulation and ROS-mediated DNA damage. Based on these considerations, 13h may be a promising antimetastatic agent for breast cancer, which is noteworthy for further exploration.
Discovery and preliminary mechanism of 1-carbamoyl β-carbolines as new antifungal candidates
Sheng, Tao,Kong, Mengmeng,Wang, Yujie,Wu, HuiJun,Gu, Qin,Chuang, Anita Shyying,Li, Shengkun,Gao, Xuewen
, (2021/06/21)
Natural β-carboline alkaloids are ideal models for the discovery of pharmaceutically important entities. Various 1-substituted β-carbolines were synthesized from commercially inexpensive tryptophan and demonstrated significant in vitro antifungal activity against G. graminis. Significantly, compound 4m (EC50 = 0.45 μM) with carboxamide at 1-position displayed the best efficacy and nearly 20 folds enhancement in antifungal potential compared to Silthiopham (EC50 = 8.95 μM). Moreover, compounds 6, 7, and 4i exhibited excellent in vitro antifungal activities and in vivo protective and curative activities against B. cinerea and F. graminearum. Preliminary mechanism studies revealed that compound 4m caused reactive oxygen species accumulation, cell membrane destruction, and deregulation of histone acetylation. These findings indicated that 1-carbamoyl β-carboline can be selected as a promising model for the discovery of novel and broad-spectrum fungicide candidates.
Design and synthesis of β-carboline derivatives with nitrogen mustard moieties against breast cancer
Bai, Jiao,Cao, Hao,Hu, Xu,Hua, Huiming,Li, Dahong,Sun, Jianan,Wang, Jiesen,Wang, Xinyan
, (2021/08/09)
To discover the promising antitumor agents, a series of β-carboline derivatives with nitrogen mustard moieties were designed and synthesized. Most target derivatives showed antiproliferative activity against MCF-7 and MDA-MB-231 cells. Among them, (1-meth
A class β . Preparation method and anti-tumor application
-
Paragraph 0027-0030, (2021/09/22)
The invention discloses β -carbofuran mustard derivatives as well as a preparation method and application thereof, and belongs to the field of natural medicines and medicinal chemistry. The invention specifically relates to a preparation method of a serie
Carboline ruthenium complex as well as preparation method and application thereof
-
Paragraph 0075; 0078-0079, (2020/10/14)
The invention provides a carboline ruthenium complex as well as a preparation method and application thereof, and belongs to the technical field of biological medicines. The series of carboline ruthenium complexes provided by the invention not only can in
Design and synthesis of β-carboline linked aryl sulfonyl piperazine derivatives: DNA topoisomerase II inhibition with DNA binding and apoptosis inducing ability
Alvala, Mallika,Godugu, Chandraiah,Kalle, Arunasree M.,Kiranmai, Gaddam,Lakshmi Manasa, Kesari,Nagendra Babu, Bathini,Nagesh, Narayana,Sagar, Arpita,Sigalapalli, Dilep Kumar,Thatikonda, Sowjanya
, (2020/07/20)
A series of new β-carboline linked aryl sulfonyl piperazine congeners have been synthesized by coupling various β-carboline acids with substituted aryl sulfonyl piperazines. Evaluation of their anticancer activity against a panel of human cancer cell lines such as colon (HT-29), breast (MDA-MB-231), bone osteosarcoma (MG-63), brain (U87 MG), prostate (PC- 3) and normal monkey kidney (Vero) cell line has been done. Among the series, compound 8ec and 8ed has shown most potent cytotoxicity with an IC50 values of 2.80 ± 0.10 μM and 0.59 ± 0.28 μM respectively against MG-63 cell line and also potent on other cell lines tested. Compounds 8ec and 8ed was found to inhibit Topo II that is confirmed by specific Topo II inhibition assay. DNA binding studies, cell cycle analysis, Annexin V study indicate that these compounds has potential anticancer activity. Molecular docking studies for compound 8ec and 8ed are incorporated to understand the nature of interaction with topoisomerase IIα and dsDNA.
1-substituted beta-carboline derivative and application thereof
-
Paragraph 0039; 0093-0095; 0096-0098, (2020/07/13)
The invention discloses 1-substituted beta-carboline derivatives and an application of the 1-substituted beta-carboline derivatives. According to the invention, beta-carboline is used as a parent nucleus; the 1-substituted beta-carboline derivatives are mainly synthesized by introducing alkyl and electron withdrawing groups at the No.1 position, agriculturally important plant pathogenic fungi andbacteria are selected, the inhibitory activity of the compound on fungi and bacteria is tested, and bacteriostatic activity test results show that the 1-substituted beta-carboline derivatives have inhibitory activity on various plant pathogenic bacteria.
Carboline derivative/analogue as well as preparation method and application thereof
-
Paragraph 0063-0064; 0069-0070, (2020/07/13)
The invention belongs to the field of chemical medicines, and provides a compound shown as a formula I or pharmaceutically acceptable salt thereof. The invention also provides analogues of the compound as shown in the formula I in the specification. Biological experiments show that the compound disclosed by the invention has anti-tumor activity and serves as a good tubulin inhibitor; the compound91b has excellent antitumor activity, can effectively promote degradation of tubulin; drug resistance caused by overexpression of beta-tubulin III and P-gp can be eliminated, and a new choice is provided for clinical medication.
