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Chemical Structure| 100-51-6 Chemical Structure| 100-51-6
Chemical Structure| 100-51-6

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Benzyl Alcohol is a monoaromatic primary alcohol widely used as a solvent and as an intermediate in cosmetic formulations, pharmaceutical and flavor/fragrance industries.

Synonyms: Benzenemethanol

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Product Citations

Product Citations      Show More

Joanna Klimek ; Oskar Kruc ; Joanna Ceklarz ; Beata Kami ´nska ; Bogdan Musielak ; Robin van der Straat , et al.

Abstract: The PD-1/PD-L1 complex is an immune checkpoint responsible for regulating the natural immune response, but also allows tumors to escape immune surveillance. Inhibition of the PD-1/PD-L1 axis positively contributes to the efficacy of cancer treatment. The only available therapeutics targeting PD-1/PD-L1 are monoclonal antibody-based drugs, which have several limitations. Therefore, small molecule compounds are emerging as an attractive alternative that can potentially overcome the drawbacks of mAb-based therapy. In this article, we present a novel class of small molecule compounds based on the terphenyl scaffold that bind to PD-L1. The general architecture of the presented structures is characterized by axial symmetry and consists of three elements: an m-terphenyl core, an additional aromatic ring, and a solubilizing agent. Using molecular docking, we designed a series of final compounds, which were subsequently synthesized and tested in HTRF assay and NMR binding assay to evaluate their activity. In addition, we performed an in-depth analysis of the mutual arrangement of the phenyl rings of the terphenyl core within the binding pocket of PD-L1 and found several correlations between the plane angle values and the affinity of the compounds towards the protein.

Keywords: PD-L1 ; immune checkpoint ; small molecule inhibitor ; cancer ; C2-symmetrical ligands

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Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto ; Prathamesh M. Datar ; Daniel J. DiRocco ; Katherine Huntera and E. Neil G. Marsh

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ∼35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

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Product Details of Benzyl alcohol

CAS No. :100-51-6
Formula : C7H8O
M.W : 108.14
SMILES Code : OCC1=CC=CC=C1
Synonyms :
Benzenemethanol
MDL No. :MFCD00004599
InChI Key :WVDDGKGOMKODPV-UHFFFAOYSA-N
Pubchem ID :244

Safety of Benzyl alcohol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Benzyl alcohol

* 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 [ 100-51-6 ]
  • Downstream synthetic route of [ 100-51-6 ]

[ 100-51-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 7379-35-3 ]
  • [ 100-51-6 ]
  • [ 49826-70-2 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 5℃; for 0.25 h;
Stage #2: at 5 - 60℃;
A flask is charged with NaH (60percent dispersion in mineral oil, 0.72 g, 18.0 mmol) then suspended in DMF (30 mL) and cooled to 5° C. To this mixture is added benzyl alcohol (1.04 mL, 10.0 mmol) drop-wise. The mixture is stirred for 15 minutes then 4-chloropyridine-HCl (1.00 g, 6.67 mmol) is added in three portions over 5 min. The resulting mixture is stirred at 5° C. for 10 min then warmed to 60° C. and stirred for 1.5 h. The mixture is then cooled to 23° C., treated with water, and extracted with EtOAc. The combined organics are dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, 5percent EtOAc in hexanes to 50percent EtOAc in hexanes) gives the title intermediate (1.10 g, 89percent).
89%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 5℃; for 0.25 h;
Stage #2: at 5 - 60℃; for 1.75 h;
Example 3
Synthesis of 4-(benzyloxy)pyridine.
A flask is charged with NaH (60percent dispersion in mineral oil, 0.72 g, 18.0 mmol) then suspended in DMF (30 mL) and cooled to 5 °C.
To this mixture is added benzyl alcohol (1.04 mL, 10.0 mmol) drop-wise.
The mixture is stirred for 15 minutes then 4-chloropyridine-HCl (1.00 g, 6.67 mmol) is added in three portions over 5 min.
The resulting mixture is stirred at 5 °C for 10 min then warmed to 60 °C and stirred for 1.5 h.
The mixture is then cooled to 23 °C, treated with water, and extracted with EtOAc.
The combined organics are dried with MgSO4, filtered, and concentrated in vacuo.
Purification of the crude by flash chromatography (SiO2, 5percent EtOAc in hexanes to 50percent EtOAc in hexanes) gives the title intermediate (1.10 g, 89percent).
References: [1] Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13756 - 13767.
[2] Patent: US2011/275627, 2011, A1, . Location in patent: Page/Page column 60.
[3] Patent: EP2331541, 2011, A1, . Location in patent: Paragraph 0070; 0071.
  • 2
  • [ 626-61-9 ]
  • [ 100-51-6 ]
  • [ 49826-70-2 ]
References: [1] Tetrahedron, 1987, vol. 43, # 11, p. 2557 - 2564.
[2] Patent: WO2010/90716, 2010, A1, . Location in patent: Page/Page column 301.
  • 3
  • [ 15854-87-2 ]
  • [ 100-51-6 ]
  • [ 49826-70-2 ]
References: [1] Tetrahedron, 2002, vol. 58, # 24, p. 4931 - 4935.
  • 4
  • [ 186519-89-1 ]
  • [ 100-51-6 ]
  • [ 16019-34-4 ]
References: [1] Tetrahedron Letters, 1998, vol. 39, # 32, p. 5685 - 5688.
  • 5
  • [ 132433-56-8 ]
  • [ 100-51-6 ]
  • [ 94777-00-1 ]
  • [ 26364-65-8 ]
References: [1] Heterocycles, 1996, vol. 42, # 1, p. 265 - 272.
  • 6
  • [ 160314-52-3 ]
  • [ 100-51-6 ]
  • [ 27591-56-6 ]
  • [ 26364-65-8 ]
References: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 19, p. 2301 - 2302.
  • 7
  • [ 73330-93-5 ]
  • [ 100-51-6 ]
  • [ 13105-53-8 ]
References: [1] Synthetic Communications, 2004, vol. 34, # 1, p. 33 - 39.
  • 8
  • [ 111-36-4 ]
  • [ 100-51-6 ]
  • [ 13105-53-8 ]
References: [1] Synthesis, 2008, # 10, p. 1612 - 1618.
  • 9
  • [ 292638-85-8 ]
  • [ 100-51-6 ]
  • [ 4126-60-7 ]
References: [1] Journal of Organic Chemistry, 1992, vol. 57, # 15, p. 4243 - 4249.
[2] Patent: WO2004/31156, 2004, A1, . Location in patent: Page 30.
[3] Patent: US2005/54707, 2005, A1, . Location in patent: Page/Page column 12.
  • 10
  • [ 2935-35-5 ]
  • [ 100-51-6 ]
  • [ 10419-67-7 ]
References: [1] Organometallics, 2014, vol. 33, # 16, p. 4269 - 4278.
  • 11
  • [ 56-84-8 ]
  • [ 100-51-6 ]
  • [ 6327-59-9 ]
References: [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6220 - 6229.
  • 12
  • [ 100-51-6 ]
  • [ 191348-16-0 ]
References: [1] Organic Letters, 2012, vol. 14, # 5, p. 1206 - 1209.
  • 13
  • [ 100-51-6 ]
  • [ 105891-54-1 ]
References: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 44, p. 8537 - 8545.
  • 14
  • [ 100-51-6 ]
  • [ 477889-91-1 ]
  • [ 1083329-33-2 ]
References: [1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333.
[2] Organic and Biomolecular Chemistry, 2009, vol. 7, # 24, p. 5103 - 5112.
 

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