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Chemical Structure| 123-08-0 Chemical Structure| 123-08-0
Chemical Structure| 123-08-0

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4-Hydroxybenzaldehyde is widely used as a raw material for polymers and pharmaceuticals. It is also a component in dendrocalamus asper bamboo shoots.

Synonyms: 4-Formylphenol; p-Formylphenol; 4-Hydroxybenzaldehyde

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Ingraham IV, Charles H ; Villanueva, Diana Polania ; Macaluso, Annamarie ; Tramuta, Annelise ; Vittori, Cecilia ; Hunter, Jean‐Jacques , et al.

Abstract: We attempt to address two key therapeutic obstacles affecting glioblastoma patients: low ability of anticancer drugs to penetrate the blood‐brain barrier (BBB), and (TMZ) resistance, by targeting mitochondrial respiration of glioblastoma cells. We designed and tested over 100 new compounds based on the chemical structure of (FF), which in its prodrug form is cytotoxic to cancer cells by causing severe impairment of mitochondrial respiration. The compounds were designed using two key predictive tools: central nervous system–multiparameter optimization (CNS‐MPO) and BBB_SCORE. These algorithms assess how effectively compounds can penetrate the BBB. We initially selected PP1 as a lead compound by testing its BBB penetration, metabolic performance, and antitumoral efficacy. PP1 accumulated in brain tumors and triggered glioblastoma cell death. However, PP1‐induced inhibition of mitochondrial respiration was followed by an immediate glycolytic response, which attenuated PP1 toxicity in a glucose‐dependent manner. To bypass this limitation, we tested two strategies: (1) the use of PP1 in combination with glycolysis inhibitors; and (2) introduction of a new compound, PP211, which inhibited mitochondrial respiration in the absence of a concomitant increase of glycolysis. Although the combination of PP1 with glycolysis inhibitors was very effective in vitro, this drug combination demonstrated elevated toxicity in mice. PP211, instead, attenuated TMZ‐resistant tumor growth and prolonged mouse survival with only minimal general animal toxicity. In summary, we developed and tested a novel mitochondria‐targeting drug candidate, PP211, which effectively crosses the BBB, overcomes TMZ resistance, and induces tumor cell death independently of glucose levels—while exhibiting minimal systemic toxicity in preclinical models. These findings support further development of PP211 for glioblastoma therapy.

Keywords: blood‐brain barrier ; drug development ; glioblastoma ; mitochondrial respiration

Purchased from AmBeed: ;

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

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

Nkomba, Gaofenngwe ; Terre' ; Blanche, Gisella ; van Rensburg, Helena Dorathea Janse ; Legoabe, Lesetja J ;

Abstract: Due to the implication of adenosine in seizure suppression, adenosine-based therapies such as adenosine receptor (AR) agonists have been investigated. This study aimed at investigating thieno[2,3 b]pyridine derivatives as non-nucleoside A1 agonists that could be used in pharmaco-resistant epilepsy (PRE). Compound 7c (thieno[2,3-b]pyridine derivative), displayed good binding a nity to the rA1 AR (Ki = 61.9 nM). This could be a breakthrough for further investigation of this heterocyclic scaffold as potential ligand. In silico evaluation of this compound raised bioavailability concerns but performed well on drug likeness tests. The effect of intramolecular cyclisation that occurs during synthesis of thieno[2,3 b]pyridines from the lead compounds, amino-3,5-dicyanopyridine derivatives ( 6a-s) in relation to AR binding was also evaluated. A signi cant loss of activity against rA1/rA2A ARs with cyclisation was revealed. Amino-3,5-dicyanopyridines exhibited greater a nity towards rA1 ARs (Ki

Keywords: Amino-3,5-dicyanopyryridines ; Thieno[2,3-b]pyridines ; Intramolecular cyclisation ; Adenosine A1/A2A receptors ; Epilepsy

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Alternative Products

Product Details of p-Hydroxybenzaldehyde

CAS No. :123-08-0
Formula : C7H6O2
M.W : 122.12
SMILES Code : O=CC1=CC=C(O)C=C1
Synonyms :
4-Formylphenol; p-Formylphenol; 4-Hydroxybenzaldehyde
MDL No. :MFCD00006939
InChI Key :RGHHSNMVTDWUBI-UHFFFAOYSA-N
Pubchem ID :126

Safety of p-Hydroxybenzaldehyde

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

Application In Synthesis of p-Hydroxybenzaldehyde

* 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.

  • Upstream synthesis route of [ 123-08-0 ]
  • Downstream synthetic route of [ 123-08-0 ]

[ 123-08-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 123-08-0 ]
  • [ 133865-89-1 ]
References: [1] Patent: CN106565520, 2017, A, .
[2] Patent: CN106220525, 2016, A, .
[3] Patent: WO2007/147491, 2007, A1, .
[4] Patent: WO2007/147491, 2007, A1, .
[5] Patent: WO2007/147491, 2007, A1, .
  • 2
  • [ 100-39-0 ]
  • [ 123-08-0 ]
  • [ 371-40-4 ]
  • [ 70627-52-0 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: at 20℃; for 12 h;
Stage #2: for 4 h; Reflux
100 ml of DMF, p-hydroxybenzaldehyde (12.2 g, 0.1 mol), potassium carbonate (16.6 g, 0.12 mol) were successively added to a 250 ml three-necked flask, Benzyl bromide (20.4 g, 0.12 mol) was added dropwise, Room temperature reaction for 12 hours, The reaction solution was poured into ice water, Solid precipitation,filter, Washed cake, The filter cake is dry. To give benzyl-protected p-hydroxybenzaldehyde (26.2 g)Yield 91percent. And then take another 250ml single neck round bottom flask, Followed by adding 100 ml of acetone, benzyl-protected p-hydroxybenzaldehyde (14.4 g, 0.05 mol), p-fluoroaniline (5.55 g, 0.05 mol) After the reaction was refluxed for 4 h, the reaction solution was cooled to 5 ° C to precipitate a solid, filter, The solid was washed with cold acetone, The solid was dried to give N-(4-fluorophenyl)-4-benzyloxybenzylideneamine (Compound IV) 14g, Yield 92percent.
References: [1] Patent: CN106397292, 2017, A, . Location in patent: Paragraph 0092; 0093.
[2] Patent: WO2008/96372, 2008, A2, . Location in patent: Page/Page column 17.
  • 3
  • [ 123-08-0 ]
  • [ 70627-52-0 ]
References: [1] Patent: JP2016/147843, 2016, A, .
  • 4
  • [ 123-08-0 ]
  • [ 403648-76-0 ]
References: [1] Journal of Fluorine Chemistry, 2001, vol. 111, # 2, p. 153 - 160.
  • 5
  • [ 76-83-5 ]
  • [ 123-08-0 ]
  • [ 892112-24-2 ]
YieldReaction ConditionsOperation in experiment
75% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 6 h; General procedure: The 4-hydroxybenzaldehyde 4 (0.8 g, 6.5 mmol) was reacted with 4-monometoxytriphenylmethyl (1.0 g, 3.2 mmol) in 10 mL of anhydrous DCM in the presence of DIEA (2.2 mL, 12.9 mmol). After 6 h at r.t., the reaction was quenched by dilution with DCM (100 mL), and the organic phase was washed three times with a solution of 0.1 M NaOH (3×100 mL). The organic phase was dried with MgSO4, and then the solvent was removed under vacuum. The crude material was then purified on a column of silica gel (70 g) suspended in hexane/EtOAc 70:30 (v/v) with 1percent of TEA, leading to product 5 (1.05 g, 82percent). 1H NMR (400 MHz, 25°C, δ, ppm in CDCl3): δ 9.76 (s, 1H), 7.57–7.25 (complex signals, 14H), 6.86 (d, J=8.5 Hz, 2H), 6.82 (d, J=8.0 Hz, 2H), 3.77 (s, 3H). 13C NMR (100 MHz, 25°C, δ, ppm in CDCl3): δ 190.7, 161.9, 158.7, 143.8, 134.9, 130.6, 130.2, 128.3, 127.8, 127.3, 120.3, 113.1, 91.1, 55.0. Product 5 (1.05 g, 2.66 mmol) was subsequently treated with 0.25 g of NaBH4 (6.60 mmol) in THF (10 mL) for 6 h at r.t. The mixture was diluted with DCM (3×100 mL), and the organic phase was washed three times with water (100 mL). The organic phase was dried with MgSO4, and then the solvent was removed under vacuum. The crude solid thus obtained was purified on a column of silica gel (70 g) suspended in hexane/EtOAc 60:40 (v/v) with 1percent of TEA. From the column was recovered 0.845 g of clean desired product 6 (2.13 mmol, 80percent). 1H NMR (400 MHz, 25°C, δ, ppm in CDCl3): δ 7.49 (d, J=6.0 Hz, 4H), 7.37–7.22 (complex signals, 8H), 6.98 (d, J=7.2 Hz, 2H), 6.79 (d, J=7.2 Hz, 2H), 6.70 (d, J=6.8 Hz, 2H), 4.45 (s, 2H), 3.75 (s, 3H). 13C NMR (100 MHz, 25°C, δ, ppm in CDCl3): δ 158.4, 155.8, 144.5, 135.6, 133.3, 130.4, 128.6, 127.6, 127.4, 126.9, 120.6, 112.8, 90.0, 64.8, 55.0. Then, 0.40 g (1.01 mmol) of product 6 was reacted with N,N-diisopropyldichlorophosphoramidite (124 μL, 0.67 mmol) in the presence of DIEA (348 μL, 2.68 mmol) in DCM (7 mL). After 1.5 h, the reaction was quenched by dilution with DCM, and the organic phase was washed three times with cold water. The organic phase was dried with MgSO4 and the solvent removed under vacuum. The material was purified with column chromatography of silica gel in hexane/EtOAc 85:15 (v/v) with 2percent of TEA. From the column was recovered 0.74 g of clean desired product (1, 87percent).
References: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 10, p. 2979 - 2988.
[2] Tetrahedron Letters, 2017, vol. 58, # 12, p. 1227 - 1229.
 

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