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Chemical Structure| 123-11-5 Chemical Structure| 123-11-5
Chemical Structure| 123-11-5

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p-Anisaldehyde (4-methoxybenzaldehyde), an extract from Pimpinella anisum seeds, exhibits antifungal activity against a number of yeast and mold strains in laboratory media, fruit purees and fruit juices.

Synonyms: p-Anisaldehyde; Anisaldehyde; 4-Anisaldehyde

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Shifali Shishodia ; Raymundo Nuñez ; Brayden P. Strohmier ; Karina L. Bursch ; Christopher J. Goetz ; Michael D. Olp , et al.

Abstract: PBRM1 is a subunit of the PBAF chromatin remodeling complex that uniquely contains six bromodomains. PBRM1 can operate as a tumor suppressor or tumor promoter. PBRM1 is a tumor promoter in prostate cancer, contributing to migratory and immunosuppressive phenotypes. Selective chemical probes targeting PBRM1 bromodomains are desired to elucidate the association between aberrant PBRM1 chromatin binding and cancer pathogenesis and the contributions of PBRM1 to immunotherapy. Previous PBRM1 inhibitors unselectively bind SMARCA2 and SMARCA4 bromodomains with nanomolar potency. We used our protein-detected NMR screening pipeline to screen 1968 fragments against the second PBRM1 bromodomain, identifying 17 hits with Kd values from 45 μM to >2 mM. Structure–activity relationship studies on the tightest-binding hit resulted in nanomolar inhibitors with selectivity for PBRM1 over SMARCA2 and SMARCA4. These chemical probes inhibit the association of full-length PBRM1 to acetylated histone peptides and selectively inhibit growth of a PBRM1-dependent prostate cancer cell line.

Nkomba, Gaofenngwe ;

Abstract: Despite the availability of various classes of antiepileptic drugs (AEDs), about one third of epileptic patients do not experience satisfactory seizure control with present treatments. This has been an important drive in the search for alternative epilepsy treatment. The endogenous nucleoside adenosine is a known anticonvulsant through activation of adenosine A1 receptors. The development of adenosine derivatives such as N6-cyclohexyladenosine (CHA) as anticonvulsants had limitations which include pronounced peripheral side effects, mainly cardiovascular effects. Over the years, non-nucleoside agonists have been investigated as an alternative set of compounds which are highly potent and selective to specific adenosine receptor (AR) subtypes. The aim of this study was to investigate the use of amino-3,5-dicyanopyridine and thieno[2,3- b]pyridine derivatives as potential A1 AR agonists. A total of 23 test compounds were synthesised (6a–s and 7a–d) and 7 of these were novel (6d and 6k–p), while 4 compounds (7a–d) have been synthesised before but have never been tested for AR affinity. The effect of intramolecular cyclisation that occurs during synthesis of thieno[2,3-b]pyridines from the intermediate compounds, amino-3,5-dicyanopyridines, in relation to AR binding was evaluated. Overall, amino-3,5-dicyanopyridine displayed superior activity towards rA1 ARs compared to thieno[2,3]pyridines. The general poor activity of thieno[2,3-b]pyridines suggest that the intramolecular cyclisation results in molecular stiffening or rigidity which negatively affects binding to the receptors, perhaps, due to steric hindrance. For instance, compound 6f (open ring) had a six-fold better inhibition constant (Ki) value of 48 nM for the A1 subtype compared to its closed ring counterpart compound 7d (rA1Ki = 305 nM). Generally, most amino-3,5- dicyanopyridines exhibited greater affinity toward the rA1 AR (Ki

Keywords: Epilepsy ; Antiepileptic drugs ; Adenosine A1/A2A receptor agonists ; Amino-3 ; 5- dicyanopyridine derivatives ; Thieno[2 ; 3-b]pyridine derivatives ; Intramolecular cyclisation

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Alternative Products

Product Details of 4-Methoxybenzaldehyde

CAS No. :123-11-5
Formula : C8H8O2
M.W : 136.15
SMILES Code : O=CC1=CC=C(OC)C=C1
Synonyms :
p-Anisaldehyde; Anisaldehyde; 4-Anisaldehyde
MDL No. :MFCD00003385
InChI Key :ZRSNZINYAWTAHE-UHFFFAOYSA-N
Pubchem ID :31244

Safety of 4-Methoxybenzaldehyde

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

Application In Synthesis of 4-Methoxybenzaldehyde

* 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 [ 123-11-5 ]
  • Downstream synthetic route of [ 123-11-5 ]

[ 123-11-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 105-13-5 ]
  • [ 104-92-7 ]
  • [ 38493-59-3 ]
  • [ 123-11-5 ]
References: [1] Journal of Organic Chemistry, 2000, vol. 65, # 12, p. 3880 - 3881.
  • 2
  • [ 123-11-5 ]
  • [ 92409-15-9 ]
References: [1] Green Chemistry, 2018, vol. 20, # 16, p. 3761 - 3771.
 

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