613-45-6|2,4-Dimethoxybenzaldehyde| Ambeed

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Quality Control of [ 613-45-6 ] Purity: 98% SDS Specification

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Design, Synthesis, and Computational Evaluation of 3, 4-Dihydroquinolin-2 (1H)-One Analogues as Potential VEGFR2 Inhibitors in Glioblastoma Multiforme

Buhlak, Shafeek ; Abad, Nadeem ; Akachar, Jihane ; Saffour, Sana ; Kesgun, Yunus ; Dik, Sevval , et al.

DOI: 10.3390/ph18020233 Pharmaceuticals,2025,18(2):233.

Abstract: Background/Objectives: Glioblastoma multiforme (GBM), an aggressive and deadly brain tumour, presents significant challenges in achieving effective treatment due to its resistance to current therapies and poor prognosis. This study aimed to synthesise and evaluate 23 novel analogues of 3,4-dihydroquinolin-2(1H)-one, designed to enhance druggability and solubility, and to investigate their potential as VEGFR2 inhibitors for GBM treatment. Methods: The synthesised compounds were analysed using in silico methods, including molecular docking and dynamics studies, to assess their interactions with key residues within the VEGFR2 binding pocket. In vitro evaluations were performed on U87-MG and U138-MG GBM cell lines using MTT assays to determine the IC50 values of the compounds. Results: Among the tested compounds, 4u (IC50 = 7.96 µM), 4t (IC50 = 10.48 µM), 4m (IC50 = 4.20 µM), and 4q (IC50 = 8.00 µM) demonstrated significant antiproliferative effects against both the U87-MG and U138-MG cell lines. These compounds exhibited markedly higher efficacy compared to temozolomide (TMZ), which showed IC50 values of 92.90 µM and 93.09 µM for U87-MG and U138-MG, respectively. Molecular docking and dynamics studies confirmed strong interactions between the compounds and VEGFR2 kinase, supporting their substantial anti-cancer activity. Conclusions: This study highlights the promising potential of 3,4-dihydroquinolin-2(1H)-one analogues, particularly 4m, 4q, 4t, and 4u, as VEGFR2-targeting therapeutic agents for GBM treatment. Further detailed research is warranted to validate and expand upon these findings.

Keywords: glioblastoma multiforme ; 3,4-dihydroquinolin-2(1H)-one ; therapeutic efficacy ; molecular docking ; molecular dynamics ; VEGFA–VEGFR2 pathway ; anti-cancer

Purchased from AmBeed: 613-45-6 ; 98-03-3 ; 54197-66-9 ; 104-88-1

Design and synthesis of imidazo[1,2-a]pyridine-chalcone conjugates as antikinetoplastid agents

Agarwal, Devesh S. ; Beteck, Richard M. ; Ilbeigi, Kayhan ; Caljon, Guy ; Legoabe, Lesetja J. ;

DOI: 10.1111/cbdd.14400 PubMed ID: 37994272 Chem. Biol. Drug Des.,2024,103(1):e14400.

Abstract: A library of imidazo[1,2-a]pyridine-appended chalcones were synthesized and characterized using 1H NMR,13C NMR and HRMS. The synthesized analogs were screened for their antikinetoplastid activity against Trypanosoma cruzi, Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense and Leishmania infantum. The analogs were also tested for their cytotoxicity activity against human lung fibroblasts and primary mouse macrophages. Among all screened derivatives, (E)-N-(4-(3-(2-chlorophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active against T. cruzi and T. b. brucei exhibiting IC50 values of 8.5 and 1.35 μM, resp. Against T. b. rhodesiense, (E)-N-(4-(3-(4-bromophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active with an IC50 value of 1.13 μM. All synthesized active analogs were found to be non-cytotoxic against MRC-5 and PMM with selectivity indexes of up to more than 50.

Keywords: antikinetoplastid ; chalcone ; drug likeliness properties ; imidazo[1,2-a]pyridine ; neglected tropical diseases (NTDs) ; Trypanosoma brucei brucei ; Trypanosoma brucei rhodesiense

Purchased from AmBeed: 613-45-6 ; 587-04-2 ; 6287-38-3 ; 1122-91-4 ; 64951-08-2 ; 99-92-3 ; 99-92-3 ; 456-48-4 ; 555-16-8 ; 94-41-7 ; 104-88-1 ; 1113-59-3 ; 459-57-4 ; 529-20-4 ; 1113-59-3

Nitrothiazole-Thiazolidinone Hybrids: Synthesis and in Vitro Antimicrobial Evaluation

Dylan Hart ; Lesetja J. Legoabe ; Omobolanle J. Jesumoroti ; Audrey Jordaan ; Digby F. Warner ; Rebecca Steventon , et al.

DOI: 10.1002/cbdv.202200729 PubMed ID: 36102043 Chem. Biodivers.,2022,19(11):e202200729.

Abstract: Herein we report the synthesis of novel compounds inspired by the antimicrobial activities of nitroazole and thiazolidin-4-one based compounds reported in the literature. Target compounds were investigated in vitro for antitubercular, antibacterial, antifungal, and overt cell toxicity properties. All compounds exhibited potent antitubercular activity. Most compounds exhibited low micromolar activity against S. aureus and C. albicans with no overt cell toxicity against HEK-293 cells nor haemolysis against human red blood cells. Notably, compound 3b exhibited low to sub-micromolar activities against Mtb, MRSA, and C. albicans. 3b showed superior activity (0.25 μg/ml) against MRSA compared to vancomycin (1 μg/ml).

Purchased from AmBeed: 613-45-6 ; 121-66-4 ; 587-04-2 ; 104-87-0 ; 6287-38-3 ; 552-89-6 ; 456-48-4 ; 830-79-5 ; 555-16-8 ; 104-88-1 ; 591-31-1 ; 3132-99-8 ; 446-52-6 ; 459-57-4 ; 529-20-4 ; 123-08-0 ; 100-52-7 ; 349121-09-1 ; 89-98-5

Product Details of [ 613-45-6 ]

CAS No. :	613-45-6
Formula :	C₉H₁₀O₃
M.W :	166.17
SMILES Code :	O=CC1=CC=C(OC)C=C1OC
MDL No. :	MFCD00003311
InChI Key :	LWRSYTXEQUUTKW-UHFFFAOYSA-N
Pubchem ID :	69175

Safety of [ 613-45-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335-H412
Precautionary Statements:	P261-P273-P305+P351+P338

Computational Chemistry of [ 613-45-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	44.81
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.06
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.91
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.52
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.83
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.98
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.66

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.25
Solubility	0.944 mg/ml ; 0.00568 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.28
Solubility	0.873 mg/ml ; 0.00526 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.59
Solubility	0.424 mg/ml ; 0.00255 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.96 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.35

Application In Synthesis of [ 613-45-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 613-45-6 ]

[ 613-45-6 ] Synthesis Path-Downstream 1~20

1
[ 939-83-3 ]
[ 613-45-6 ]
[ 106987-30-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 485 - 488.
[2]Journal fur praktische Chemie (Leipzig 1954),1925,vol. <2> 109,p. 221.
Justus Liebigs Annalen der Chemie,1925,vol. 441,p. 248.

2
[ 22312-62-5 ]
[ 613-45-6 ]
[ 143424-14-0 ]

References: [1]Pharmaceutical Chemistry Journal,1992,vol. 26,p. 245 - 249.
Khimiko-Farmatsevticheskii Zhurnal,1992,vol. 26,p. 48 - 51.

3
[ 22838-46-6 ]
[ 613-45-6 ]
methyl (E)-3-(2,4-dimethoxybenzylidenamino)-3-phenylpropionate [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 10287 - 10290.

4
[ 92138-20-0 ]
[ 613-45-6 ]
[ 956291-36-4 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6937 - 6941.

5
[ 35613-44-6 ]
[ 613-45-6 ]
[ 1198328-58-3 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 9222 - 9224.

6
[ 2799-07-7 ]
[ 613-45-6 ]
[ 1245517-12-7 ]

References: [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3723 - 3733.

7
[ 19012-02-3 ]
[ 613-45-6 ]
[ 27664-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In water; at 60℃; for 12h;	General procedure: To a solution of N-methyl-3-acetylindol (1 mmol) and the benzaldehyde derivative (1 mmol) in methanol (10 ml) was added KOH (1 ml from a 50% solution in H2O). The mixture was heated at 60 C for 12 h then evaporated to dryness. The crude was dissolved in ethyl acetate (30 ml) then washed with HCl (1N, 10 ml) and H2O (10 ml), respectively. The organic layer was separated, dried over Na2SO4 and evaporated. The product was purified by chromatography column eluted with hexane:ethyl acetate (8:2) to yield the title compound as a yellow powder.

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3193 - 3200.
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6143 - 6148.

8
[ 36062-04-1 ]
[ 613-45-6 ]
[ 57-13-6 ]
[ 1432038-17-9 ]

Yield	Reaction Conditions	Operation in experiment
27%		General procedure: To a solution of the corresponding aromatic aldehyde (0.27 mmol) in EtOH (0.5 mL) was added urea (0.54 mmol) and CuSO4·5H2O (0.054 mmol). The mixture was stirred at 80 °C for 15 minutes before tetrahydrocurcumin or tetrahydrodemethoxycurcumin (0.27 mmol) was added. The reaction mixture was continued stirring for 24 hours and quenched with water (2 mL). The solution was washed with water (10 mL) and extracted with EtOAc (415 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated under reduced pressure to afford crude product as a yellow brown oil. Purification was accomplished by column chromatography eluting with 60percent-75percent EtOAc/hexane to furnish compounds 8-17.

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2880 - 2882.

9
[ 2247-88-3 ]
[ 613-45-6 ]
[ 1436852-90-2 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 5705 - 5710.

10
[ 1403898-64-5 ]
[ 613-45-6 ]
[ 1605312-93-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃;	Preparation 46: (2R,5R) -4-(2,4-Di methoxy-benzyl)-5-hydroxymethyl-2-methyl-pi perazi ne1-carboxylic acid tert-butyl ester To an ice-cooled solution of (2R ,5R)-5-hydroxymethyl-2-methyl-piperazine- 1 -carboxylic acid tert-butyl ester (10.0 g, 43.5 mmol) in DOE (70 mL) were added 2,4-dimethoxy-benzaldehyde (11.1 g, 66.6 mmol) and sodium triacetoxyborohydride(11.1 g, 52.2 mmol) in small portions. Thereaction mixture was stirred at room temperature overnight. Saturated aqueous NaHCO3 was added and the product was extracted with DCM. The organic phase was dried and evaporated. Chromatography on silica gel, eluting with petrol - EtOAc 0-50% gave the title compound (16.3 g, 99%). 1297-012-1 MS: [M+H] = 381.

References: [1]Patent: WO2014/60767,2014,A1 .Location in patent: Page/Page column 127; 128.
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 7314 - 7329.

11
[ 1597-32-6 ]
[ 613-45-6 ]
[ 1607485-74-4 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In toluene; at 135℃;	101381 To a flask containing commercially available 2-Amino-6-fluoropyridine (iO.2 g, 9i mmol) & commercially available 2,4-dimethoxybenzaldehyde (i5.4 g, 93 mmol) was added anhydrous toluene (300 mL), then TFA (i ml, i2.98 mmol). The reaction mixture was then heated to i35C while stirring in the hood with an water cooled reflux condenser attached to a Dean Stark trap. Followed by LC/MS. Heated overnight, then cooled to room temperature, then concentrated to yield crude N-(2,4-dimethoxybenzylidene)-<strong>[1597-32-6]6-fluoropyridin-2-amine</strong> (2-1).
	With trifluoroacetic acid; In toluene; at 135℃; for 18h;Dean-Stark;	To a flask containing commercially-available <strong>[1597-32-6]2-amino-6-fluoropyridine</strong> (2-1, 10.2 g, 91 mmol)and commercially-available 2,4-dimethoxybenzaldehyde (1-2, 15.4 g, 93 mmol) was addedanhydrous toluene (300 mL) followed by TFA (1 mL, 12.98 mmol). The reaction mixture wasthen heated to 135 C while stirring with a water-cooled reflux condenser attached to a DeanStark trap. After 18 h, the reaction mixture was cooled to room temperature and concentrated togive N-(2, 4-dimethoxybenzylidene)-<strong>[1597-32-6]6-fluoropyridin-2-amine</strong> (2-2). Carried forward withoutfurther purification.

References: [1]Patent: WO2014/66490,2014,A1 .Location in patent: Paragraph 0138.
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2683 - 2688.

12
[ 103-82-2 ]
[ 599-67-7 ]
[ 528-75-6 ]
[ 60-12-8 ]
[ 106-47-8 ]
[ 126-30-7 ]
[ 613-45-6 ]
[ 530-48-3 ]
[ 102-20-5 ]
[ 1620217-69-7 ]
[ 354538-08-2 ]