203717-13-9Relevant articles and documents
Iodine Catalysed Synthesis of Luminescent β-Carboline Tethered Thiazolo[4,5-c]carbazole and Naphtho[2,1-d]thiazole Derivatives and Estimation of their Light Emitting Properties
Awasthi, Pamita,Singh, Manpreet,Singh, Virender
, (2020)
A Simple, convenient and highly efficient I2-catalysed approach has been unfolded towards the synthesis of highly fluorescent β-carboline C-1(3)-tethered thiazolo[4,5-c]carbazoles, naphtho[2,1-d]thiazoles and benzothiazole derivatives using Kumujian C as a template. This domino strategy proceeds through assembly of 1-formyl-9H-β-carbolines, arylamines and elemental sulfur via formation of one C–N and two C–S bonds in a single operation. Importantly, the methodology was found applicable to β-carboline acetals also. A diversely substituted library of 37 β-carboline tethered arylthiazole hybrids was prepared in excellent yields. The strategy was found appropriate for gram scale synthesis also. The photophysical properties of these fluorophores were also estimated and showed excellent fluorescence properties with quantum yield (ΦF) up to 92 %.
A transition metal-free approach towards the regioselective synthesis of β-carboline tethered pyrroles and 2,3-dihydro-1: H -pyrroles
Singh, Manpreet,Paul, Avijit Kumar,Singh, Virender
, p. 12370 - 12383 (2020/07/30)
An efficient metal-free approach has been devised for the synthesis of novel β-carboline C-1 tethered 2,3-dihydropyrroles and pyrroles via one-pot assembly involving 1-formyl β-carbolines, aryl methyl ketones, and isonitriles. The reaction advances through the formation of β-carboline linked enones followed by [3+2] cycloaddition with isonitriles. This methodology features an operationally simple procedure, multicomponent character, high atom economy, a broad substrate scope, short reaction times, and high regioselectivity with excellent yields. The scope of the process was exemplified via the synthesis of a library of 34 novel compounds with significant diversity.
Molecular hybrid design, synthesis, in vitro and in vivo anticancer evaluation, and mechanism of action of N-acylhydrazone linked, heterobivalent β-carbolines
Chen, Wei,Chen, Xiaofei,Dai, Bin,Fan, Wenxi,Guo, Liang,Ma, Qin,Zhang, Jie
, (2020/02/05)
A series of N-acylhydrazone-linked, heterobivalent β-carboline derivatives was designed and synthesized from L-tryptophan in a nine-step reaction sequence. The effort resulted in the heterobivalent β-carbolines 10a–t in good yields. The target compounds were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). The in vitro cytotoxic activity of the synthesized compounds was evaluated against normal EA.HY926 cells and five cancer cell lines: LLC (Lewis lung carcinoma), BGC-823 (gastric carcinoma), CT-26 (murine colon carcinoma), Bel-7402 (liver carcinoma), and MCF-7 (breast carcinoma). Compound 10e, with an IC50 value of 2.41 μM against EA.HY926 cells, was the most potent inhibitor. It showed cytotoxicity against all five cancer cell lines of different origin – murine and human, with IC50 values ranging from 4.2 ± 0.7 to 18.5 ± 3.1 μM. A study of structure-activity relationships indicated that the influence on cytotoxic activities of the substituent in the R9′-position followed the tendency, 2,3,4,5,6-perfluorophenylmethyl > 4-fluorobenzyl > 3-phenylpropyl group. The antitumor efficacies of the selected compounds were also evaluated in mice. Compound 10e exhibited potent antitumor activity, with tumor inhibition of more than 40% for Sarcoma 180 and 36.7% for Lewis lung cancer. Furthermore, the pharmacological mechanisms showed that compound 10e has a certain impairment in the motility of LLC cells, which suggests the anti-metastatic potential. And compound 10e inhibited angiogenesis in chicken chorioallantoic membrane assay, and the anti-angiogenetic potency was more potent than the reference drug combretastatin A4-phosphate (CA4P) at a concentration 50 μM.
A metal-free approach towards synthesis of β-carboline C1 substituted Pyrido(2,3-c)carbazole derivatives (nitramarine analogues) through A3-coupling and estimation of their light emitting properties
Singh, Manpreet,Vaishali,Kumar, Sunit,Jamra, Rahul,Pandey, Satyendra K.,Singh, Virender
supporting information, (2020/10/20)
A simple and efficient metal-free methodology is presented to access fluorescent β-carboline tethered pyrido(2,3-c)carbazole derivatives (Nitramarine analogues) via A3-coupling of 1-formyl-9H-β-carbolines, 3-amino-9-ethylcarbazole, and terminal
In(OTf)3 catalysed an expeditious synthesis of β-carboline-imidazo[1,2-: A] pyridine and imidazo[1,2- a] pyrazine conjugates
Devi, Nisha,Singh, Dharmender,Honey,Mor, Satbir,Chaudhary, Sandeep,Rawal, Ravindra K.,Kumar, Vipin,Chowdhury, Asim K.,Singh, Virender
, p. 43881 - 43891 (2016/06/09)
β-Carboline containing alkaloids are ubiquitously present in Nature, while imidazo[1,2-a]pyridine nucleus is incorporated in various synthetic commercial drugs and biologically previliged moieties. On this basis, new β-carboline-imidazoazine conjugates were designed and a small library of compounds integrating both the pharmacophores was constructed with 4-points of diversity by using the In(OTf)3 assisted Groebke-Blackburn-Bienayme multicomponent strategy. The methodology was found to be simple and convenient for the efficient syntheses of β-carboline-imidazo[1,2-a]azine conjugates. The present synthetic protocol provides several advantages like operational simplicity, appreciable atom economy, short reaction time and easy purification procedure.
Synthesis and biological evaluation of novel alkyl diamine linked bivalent β-carbolines as angiogenesis inhibitors
Chen, Wei,Zhang, Guoxian,Guo, Liang,Fan, Wenxi,Ma, Qin,Zhang, Xiaodong,Du, Runlei,Cao, Rihui
, p. 249 - 261 (2016/09/09)
We have synthesized and evaluated a series of novel alkyl diamine linked bivalent β-carbolines as potent angiogenesis inhibitors. The results demonstrated that most bivalent β-carbolines exhibited significant antiproliferative effects against human umbilical vein cell lines EA.HY926. Compound 4m was found to be the most potent antiproliferative agent with IC50value of 2.16?μM against EA.HY926?cell lines. Mechanism investigations revealed that compound 4m could significantly inhibit EA.HY926?cells migration and tube formation in a dose-dependent manner. Moreover, compound 4m also showed obvious angiogenesis inhibitory effects in CAM assay, and the antiangiogenetic potency was more potent than the reference drug Endostar. The bivalent β-carbolines might be served as candidates for the development of vascular targeting antitumor drugs.
Synthesis and biological evaluation of 1,9-disubstituted β-carbolines as potent DNA intercalating and cytotoxic agents
Chen, Zhiyong,Cao, Rihui,Shi, Buxi,Guo, Liang,Sun, Jie,Ma, Qin,Fan, Wenxi,Song, Huacan
, p. 5127 - 5137 (2011/11/28)
A series of novel 1,9-disubstituted β-carbolines was designed, synthesized and evaluated as cytotoxic and DNA intercalating agents. Compounds 7b, 7c, 8b and 8c exhibited the most potent cytotoxic activities with IC 50 values of lower than 20 μM against ten human tumor cell lines. The results indicated that (1) the 3-chlorobenzyl and 3-phenylpropyl substituents in position-9 of β-carboline nucleus were the suitable pharmacophoric group giving rise to significant antitumor agents; (2) the length of the alkylamino side chain moiety affected their cytotoxic potencies, and three CH2 units were more favorable. In addition, these compounds were found to exhibit remarkable DNA intercalating effects.
Synthesis of cytotoxic 1-polyhydroxyalkyl-β-carboline derivatives
Abdel-Moty,Sakai,Aimi,Takayama,Kitajima,El-Shorbagi,Ahmed,Omar
, p. 1009 - 1017 (2007/10/03)
dl-1-(1-Oxo-3,4-threo-3,4,5-trihydroxy-1-pentyl)-β- carboline 16a was synthesized from 1-formyl-β-carboline in 13 steps. The prepared compound is one of the diastereomers of an alkaloid 3 produced by the inter-generic somatic hybrid cell culture of Rauwolfia serpentina Benth and Rhazya stricta Decaisne (family: Apocynaceae). The N9-benzyl and N9-methyl derivatives 16b,c were also prepared. The final compounds and some of the intermediates showed cytotoxic activity against human promyelocytic leukemia cells HL 60 and/or human diploid embryonic lung fibroblast cells.
