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[ CAS No. 456-48-4 ] {[proInfo.proName]}

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Chemical Structure| 456-48-4
Chemical Structure| 456-48-4
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Product Citations

Product Citations      Expand+

Jooste, Joelien ; Legoabe, Lesetja J ; Ilbeigi, Kayhan , et al. DOI: PubMed ID:

Abstract: Geraniol, a primary component of several essential oils, has been associated with broad-spectrum antiprotozoal activities, although moderate to weak. This study primarily concentrated on the synthesis of hydrazinated geraniol derivatives aspotential antiprotozoal agents. The synthesised compounds were tested in vitro against different parasitic protozoans of clinical relevance, including Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense, Trypanosoma cruzi and Leishmania infantum. Compounds 6, 8, 13, 14 and 15 demonstrated low micromolar activity against the different parasites. Compounds 8, 13, 14 and 15 had the highest efficacy against Trypanosoma brucei rhodesiense, as indicated by their respective IC50 values of 0.74, 0.56, 1.26 and 1.00 μM. Compounds 6, 14 and 15 displayed the best activity against Trypanosoma brucei brucei, with IC50 values of 1.49, 1.48 and 1.85 μM, respectively. The activity of compounds 6, 14 and 15 also extended to intracellular Trypanosoma cruzi, with IC50 values of 5.14, 6.30 and 4.90 μM, respectively. Compound 6, with an IC50 value of 11.73 μM, and compound 14, with an IC50 value of 8.14 μM, demonstrated some modest antileishmanial activity.

Keywords: geraniol ; Leishmania infantum ; Trypanosoma brucei brucei ; Trypanosoma brucei rhodesiense ; Trypanosoma cruzi

Purchased from AmBeed: ; ; ; ;

Agarwal, Devesh S. ; Beteck, Richard M. ; Ilbeigi, Kayhan , et al. DOI: PubMed ID:

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 ; ; drug likeliness properties ; ; neglected tropical diseases (NTDs) ; Trypanosoma brucei brucei ; Trypanosoma brucei rhodesiense

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; 1113-59-3

Michael B. Dybek ;

Abstract: Memantine, an N-methyl-D-aspartate receptor (NMDAR) antagonist is FDA approved for the treatment of moderate to severe Alzheimer disease. The efficacy is believed to stem from its ability to block/mitigate excitotoxicity that stems from excessive glutamatergic activation/transmission and is thus neuroprotective. However, they display tolerability issues that hinder their ability to be utilized as neuroprotective agents. Previous studies from our lab suggest that the compounds that function as uncompetitive NMDAR antagonists and have moderate affinity to the NMDAR demonstrate the best tolerability. This observation has prompted investigations for novel neuroprotective NMDAR antagonists with improved efficacy and tolerability. Our lead compounds phencyclidine (PCP) and analogs have demonstrated the ability to protect hippocampal neurons from NMDA insult in vitro. Our studies explored synthesizing and evaluating both arylalkylamines and 1,2-diarylethylamines. A total of 76 target compounds were synthesized as part of this exploration. In vitro competitive radio-ligand binding assays were conducted for each compound to determine affinities to NMDAR in rat forebrain homogenate. Several of these compounds demonstrated binding affinities within a previously defined target range (400 nM – 2,100 nM). This range was previously determined to provide the highest tolerability for uncompetitive NMDAR antagonists. 34 compounds were further evaluated to obtain binding affinities on 44 other relevant central nervous system targets. This SAR investigation has uncovered several intriguing polypharmacological profiles have emerged, including potent affinities to NMDAR, dopamine transporter (DAT), norepinephrine transporter (NET), and serotonin transporter (SERT).

Purchased from AmBeed: ; ; ;

Dylan Hart ; Lesetja J. Legoabe ; Omobolanle J. Jesumoroti , et al. DOI: PubMed ID:

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: ; ; ; ; ; ; ; ; ; 591-31-1 ; ; ; ; ; ; 123-08-0 ; 100-52-7 ; ; 89-98-5

Product Details of [ 456-48-4 ]

CAS No. :456-48-4 MDL No. :MFCD00003348
Formula : C7H5FO Boiling Point : -
Linear Structure Formula :(COH)C6H4F InChI Key :PIKNVEVCWAAOMJ-UHFFFAOYSA-N
M.W : 124.11 Pubchem ID :68009
Synonyms :

Calculated chemistry of [ 456-48-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 31.79
TPSA : 17.07 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : 1.75
Log Po/w (WLOGP) : 2.06
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 2.42
Consensus Log Po/w : 1.91

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.14
Solubility : 0.901 mg/ml ; 0.00726 mol/l
Class : Soluble
Log S (Ali) : -1.73
Solubility : 2.33 mg/ml ; 0.0188 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.326 mg/ml ; 0.00262 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 456-48-4 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P305+P351+P338 UN#:1989
Hazard Statements:H225-H315-H319-H335 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 456-48-4 ]

* 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 [ 456-48-4 ]

[ 456-48-4 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 57497-39-9 ]
  • [ 456-48-4 ]
  • [ 139607-30-0 ]
  • 2
  • [ 2612-28-4 ]
  • [ 456-48-4 ]
  • [ 202476-48-0 ]
YieldReaction ConditionsOperation in experiment
With PTS; In toluene; Step 1 : 2-Propyl-1,3-propanediol (138.0 g; 1.17 mol) and 3-fluorobenzaldehyde (138.0 g; 1.11 mol) were dissolved in toluene (1.5 liters), and PTS (7 g) was added. The mixture was refluxed for 3 hours while being dehydrated with a Dean-Stark's device. The resultant reaction mixture was washed sequentially with saturated sodium bicarbonate solution and saturated brine, and then dried over magnesium sulfate. Subsequently, the solvent was evaporated. The residue was recrystallized twice from heptane, to thereby obtain 81.2 g (362 mmol) of 5-propyl-2-(3-fluorophenyl)-1,3-dioxane. The yield of the compound from 3-fluorobenzaldehyde was 32.6%.
  • 3
  • [ 120-35-4 ]
  • [ 456-48-4 ]
  • 4-Methoxy-3-(3-fluoro-benzylamino)-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 214 4-Methoxy-3-(3-fluoro-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-fluorobenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 137-140 C.
  • 4
  • [ 456-48-4 ]
  • [ 97682-44-5 ]
  • 5
  • [ 5676-56-2 ]
  • [ 456-48-4 ]
  • C15H9BrFNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In dichloromethane; water;Inert atmosphere; General procedure: The SBOs were prepared by the base-catalysed condensation of the appropriate 5-halogeno-2-methylbenzoxazole with the requisite aromatic aldehyde under phase transfer conditions. In a typical experiment, equimolar quantities (5 mmol) of the starting materials were dissolved in dichloromethane (20-50 ml) in the presence of benzyltriethylammonium chloride (3 mmol) and stirred magnetically under a nitrogen atmosphere as an aqueous solution of sodium hydroxide (50%, w/v, 5 ml) was added dropwise over a period of 10 min. After being stirred for 2-36 h until analytical thin layer chromatography indicated that the reaction was complete, the mixture was diluted with water (50 ml) and the SBO was extracted with dichloromethane (3×20 ml), dried (MgSO4), filtered, evaporated under reduced pressure and recrystallized from aqueous methanol or ethanol.
  • 6
  • [ 57497-39-9 ]
  • [ 456-48-4 ]
  • [ 139607-30-0 ]
  • 7
  • [ 39549-79-6 ]
  • [ 456-48-4 ]
  • 2-(3-fluorophenyl)-7-methylquinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With sodium hydrogensulfite; In N,N-dimethyl acetamide; at 150℃; General procedure: Sodium hydrogen sulfite (4 mmol) was added to a solution of anthranilamide 1 (2 mmol) and benzaldehyde 2 (2 mmol) in N,N- dimethylacetamide (5 mL). The mixture was heated under continuous stirring at 150 o C for 2-3 h and poured into ice water. The precipitate was then filtered, washed with water followed byethanol, and dried to yield the 2-arylquinazolinones 3-31.#10;#10;
  • 8
  • [ 141-82-2 ]
  • [ 456-48-4 ]
  • [ 19883-77-3 ]
  • 9
  • [ 456-48-4 ]
  • [ 19883-77-3 ]
  • 10
  • [ 456-48-4 ]
  • (R)-3-amino-3-(3-fluoro-phenyl)-propionic acid [ No CAS ]
  • [ 20595-30-6 ]
  • [ 19883-77-3 ]
  • 11
  • [ 456-48-4 ]
  • (R)-3-amino-3-(3-fluoro-phenyl)-propionic acid [ No CAS ]
  • [ 723284-79-5 ]
  • [ 20595-30-6 ]
  • [ 19883-77-3 ]
  • 12
  • [ 54396-44-0 ]
  • [ 868-85-9 ]
  • [ 456-48-4 ]
  • dimethyl (3-fluorophenyl)(2-methyl-3-(trifluoromethyl)phenylamino)methylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With chitosan; In neat (no solvent); at 75℃; for 0.0833333h;Microwave irradiation; Green chemistry; General procedure: An equimolar mixture of <strong>[54396-44-0]2-methyl-3-(trifluoromethyl)aniline</strong> (0.351 g, 0.002 mol), corresponding aldehyde (0.002 mol), dimethyl phosphite (0.18 ml, 0.002 mol) and chitosan catalyst (10 molpercent) were taken in a reaction glass tube, degassed for 10 min and microwave irradiated at 180 W for 2 min at 60 °C. The progress of the reaction was monitored by TLC using petroleum ether and ethyl acetate (3:7) as solvent. After completion of the reaction, the mixture was diluted with ethyl acetate, washed with water (2 x 15 ml) followed by brine (1 x 10 ml), dried over Na2SO4 and evaporated to dryness. The crude mass was purified by column chromatography on silicagel (100-200 mesh) by using a 7:3 mixture of ethyl acetate in hexane to afford the pure alpha-aminophosphonates.
  • 13
  • [ 1986-47-6 ]
  • [ 456-48-4 ]
  • (1S*,2R*)-N-(3-fluorobenzyl)-2-phenylcyclopropan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound.
  • 14
  • [ 456-48-4 ]
  • [ 703-67-3 ]
  • 15
  • [ 405939-39-1 ]
  • [ 456-48-4 ]
  • tert-butyl 4-bromo-5-((3-fluorophenyl)(hydroxy)methyl)thiazol-2-ylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% To a solution of lithium diisopropylamide (16.5 ml_, 33 mmol) in tetrahydrofuran (20 ml_) at 0 C was added ferf-butyl 5-bromothiazol-2-ylcarbamate (2.8 g, 10.0 mmol) slowly under argon. The reaction mixture was stirred at 0 C for 30 minutes before a solution of 3-fluorobenzaldehyde (4.1 g, 33.0 mmol) in tetrahydrofuran (1 0 ml_) was added. The reaction solution was warmed to room temperature and stirred for 20 h. The reaction mixture was diluted with water (30 ml_) and extracted with ethyl acetate (150 ml_ x 3). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 4/1 ) to give ferf-butyl 4-bromo-5-((3-fluorophenyl)(hydroxy)methyl)thiazol-2-ylcarbamate as a yellow solid (2.5 g, 6.2 mmol, 62%). LCMS (ESI) m/z: 346.9 [M-56+H]+.
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