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[ CAS No. 3731-52-0 ] {[proInfo.proName]}

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Chemical Structure| 3731-52-0
Chemical Structure| 3731-52-0
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Ingraham, Charles H. IV ; Stalinska, Joanna ; Carson, Sean C. , et al. DOI: PubMed ID:

Abstract: Glioblastomas are highly aggressive brain tumors for which therapeutic options are very limited. In a quest for new anti-glioblastoma drugs, we focused on specific structural modifications to the benzoyl-phenoxy-acetamide (BPA) structure present in a common lipid-lowering drug, fenofibrate, and in our first prototype glioblastoma drug, PP1. Here, we propose extensive computational analyses to improve the selection of the most effective glioblastoma drug candidates. Initially, over 100 structural BPA variations were analyzed and their physicochemical properties, such as water solubility (- logS), calculated partition coefficient (ClogP), probability for BBB crossing (BBB_SCORE), probability for CNS penetration (CNS-MPO) and calculated cardiotoxicity (hERG), were evaluated. This integrated approach allowed us to select pyridine variants of BPA that show improved BBB penetration, water solubility, and low cardiotoxicity. Herein the top 24 compounds were synthesized and analyzed in cell culture. Six of them demonstrated glioblastoma toxicity with IC50 ranging from 0.59 to 3.24 μM. Importantly, one of the compounds, HR68, accumulated in the brain tumor tissue at 3.7 ± 0.5 μM, which exceeds its glioblastoma IC50 (1.17 μM) by over threefold.

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Product Details of [ 3731-52-0 ]

CAS No. :3731-52-0 MDL No. :MFCD00006412
Formula : C6H8N2 Boiling Point : No data available
Linear Structure Formula :NH2CH2C5H4N InChI Key :HDOUGSFASVGDCS-UHFFFAOYSA-N
M.W : 108.14 Pubchem ID :31018
Synonyms :
Chemical Name :Pyridin-3-ylmethanamine

Safety of [ 3731-52-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405 UN#:2735
Hazard Statements:H314 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 3731-52-0 ]

* 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 [ 3731-52-0 ]

[ 3731-52-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 3731-52-0 ]
  • [ 154775-43-6 ]
  • [ 204574-45-8 ]
YieldReaction ConditionsOperation in experiment
95% With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25℃; for 20h; Step C. N-(3-Pyridylmethyl)-1-tert-butoxycarbonyl-4-piperidinepropanamide 1-tert-Butoxycarbonyl-4-piperidinepropionic acid (2g, 7.77mmoles), 3-(aminomethyl)pyridine (1.029ml, 10.1mmoles), DEC.HCl (1.937g, 10.1 mmoles), HOBT (1.365g, 10.1 mmoles) and NMM (1.111 ml, 10.1 mmoles) are dissolved in anhydrous DMF (25ml) and the mixture is stirred under argon at 25C for 20h. The solution is evaporated to dryness and the residue is taken up in dichloromethane, washed with 0.3N NaOH, dried over magnesium sulfate, filtered and evaporated to dryness. The residue is chromatographed on silica gel using 1.5%-2.5% (10% conc. ammonium hydroxide in methanol)-dichloromethane as the eluant to give the title compound (2.555g, 95%), ESIMS: m/z 348.1 (MH+).
  • 2
  • [ 3731-52-0 ]
  • [ 1022980-69-3 ]
  • [ 1022980-73-9 ]
  • 3
  • [ 3731-52-0 ]
  • [ 21512-16-3 ]
  • [ 1437787-03-5 ]
  • 4
  • [ 3731-52-0 ]
  • [ 1397-89-3 ]
  • amphotericin B 3-pyridylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.09% With diphenyl phosphoryl azide; triethylamine; In N,N-dimethyl acetamide; at 20℃;Darkness; Inert atmosphere; Example 9 Synthesis of Amide 9: (3-pyridylamide) of AmB In another preferred embodiment the present invention provides the analogue of AmB denominated amide 9, represented by formula IX; using amphotericin B, N,N-dimethylacetamide, triethylamine, 3-aminomethylpyridine and diphenizphosphorylazide as starting materials. In a 100 mL flask ball 462 mg (0.5 mmol) amphotericin B were weighed and dissolved in 10 mL de N,N-dimethyl acetamide. The flask was wrapped in aluminum foil as amphotericin B decays in the presence of sunlight; the reaction was performed under nitrogen atmosphere. Subsequently 0.7 mL (5.0 mmol) of triethylamine, 5.0 mmol of 3-aminomethylpyridine and 1.08 mL (5.0 mmol) of diphenizphosphorylazide were added. The reaction was left at room temperature with constant stirring until disappearance of the raw material (amphotericin B). The progress of the reaction was measured by thin layer chromatography in the system chloroform:methanol:water (20:10:1). Subsequently, the reaction was precipitated in 150 mL of anhydrous ethyl ether and let to stand until the product precipitated completely, which is normally associated with the clearance of the ether solution. Ethyl ether was decanted and the precipitate formed was dissolved in 1-butanol and washed twice with 50 mL of distilled water. Subsequently, 1-butanol was evaporated under reduced pressure (10 mmHg) at 25 C. Finally, the derivative was precipitated with 50 mL of ethyl ether and washed three times with 50 mL of ethyl ether and once with 50 mL of hexane. The product was vacuum dried. In this reaction, the analogue 9 was obtained with a 95.09% yield after product purification.
  • 5
  • [ 3731-52-0 ]
  • [ 56844-12-3 ]
  • 6-(2-methoxyphenyl)-N-(pyridin-3-ylmethyl)thieno[2,3-d]pyrimidin-4-amine [ No CAS ]
  • 6
  • [ 3731-52-0 ]
  • [ 56844-12-3 ]
  • 6-bromo-N-(pyridin-3-ylmethyl)thieno[2,3-d]pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In isopropyl alcohol; at 80℃; for 1h;Inert atmosphere; General procedure: Compound 1 (1.00 g, 4.01 mmol) was mixed with the benzylamine (2-3 eq.) and i-PrOH (2-10 mL) and agitated at 80 C for 1-50 h, under nitrogen atmosphere. Then the mixture was cooled to rt, concentrated in vacuo, diluted with water (50 mL) and diethyl ether (100 mL) or EtOAc (100 mL). After phase separation, the water phase was extracted with more diethyl ether (2×50 mL) or EtOAc (2×50 mL). The combined organic phases were washed with saturated aq NaCl solution (25-50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude oil was purified by drying under reduced pressure to constant weight, by silica-gel column chromatography or crystallized as specified for each individual compound.
  • 7
  • [ 3731-52-0 ]
  • [ 4876-10-2 ]
  • 4-((pyridin-3-ylmethylamino)methyl)quinolin-2(1H)-one [ No CAS ]
  • 8
  • [ 3731-52-0 ]
  • [ 75-15-0 ]
  • [ 13304-62-6 ]
  • 3-(benzylamino)-3-oxopropyl ((pyridin-3-yl)methyl)carbamodithioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% General procedure: To a mixture of pyridin-3-ylmethanamine 18 (108 mg, 1 mmol),TEA (100 mg, 1 mmol) in water (10 mL), CS2 (91 mg, 1.2 mmol) was added dropwise. After stirring for 5 min, the corresponding halide19 (1 mmol) or Michael acceptor 20 (1 mmol) was added. The reaction mixture was stirred at room temperature for 2 h, then extracted with ethyl acetate (30 mL 3). The organic phase was combined and dried over Na2SO4, concentrated under vacuum and purified by column chromatography on silica gel or recrystallization (ethyl acetate/petroleum ether) to afford the corresponding compound 17
  • 9
  • [ 3731-52-0 ]
  • [ 4506-66-5 ]
  • 2,6-di(3-pyridyl) benzo[1,2-d:4,5-d’]bisimidazole [ No CAS ]
  • 10
  • [ 3731-52-0 ]
  • [ 4865-84-3 ]
  • 2-(benzo[d]isoxazol-3-yl)-N-(pyridin-3-ylmethyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; General procedure: To an ice cold solution of <strong>[4865-84-3]1,2-benzisoxazol-3-acetic acid</strong> 8 (1.0 mmol, 1.0 eq.), N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (1.5 mmol, 1.5 eq.), and 1-hydroxybenzotriazole (1.0 mmol, 1.0 eq) in DCM (25 mL) was added solution of TFA salt of proline derivative/3-aminomethyl pyridine/compound 10 (1.0 mmol, 1.0 eq.) and triethylamine (2.5 mmol, 2.5 eq.) in DCM (5 mL). The reaction mixture was stirred at 0-5 C for 30 min and at room temperature for overnight. The completion of the reaction was monitored using TLC analysis using pet.ether:ethyl acetate (1:1). The reaction mixture was concentrated on a rotavapor to give crude residue. The residue was dissolved in ethyl acetate (50 mL) and was washed with water (225 mL), 0.5N HCl solution (210 mL), saturated NaHCO3 (215 mL), and brine (20 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and concentrated to give crude compound. The compounds were purified by column chromatography using petether: ethyl acetate from 9:1 to 2:8 to give pure compounds 9a-d and 11a-e solid.
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