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Chemical Structure| 60811-24-7 Chemical Structure| 60811-24-7

Structure of 3,4-Difluorothiophenol
CAS No.: 60811-24-7

Chemical Structure| 60811-24-7

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Product Citations

Product Citations

Hwang, Dong-Jin ; Yang, Chuanhe ; Wang, Yinan ; Kelso, Hannah ; Pochampally, Satyanarayana ; Pfeffer, Lawrence M , et al.

Abstract: Background/Objectives: Human glioblastoma (GBM) is the most aggressive brain cancer in adults and a highly treatment-refractory malignancy. The overall prognosis for the GBM is extremely poor, with a median survival of 12–14 months after initial diagnosis. Many GBM patients initially respond to the DNA alkylating agent temozolomide (TMZ), but patients often become therapy-resistant, and tumors recur. We previously reported that treatment with PFI-3, which is a small molecule inhibitor of the bromodomain of the BRG1 subunit of the SW1/SNF chromatin remodeling complex, enhanced the sensitivity of GBM cells to TMZ in vitro and in vivo GBM animal models. Our general objective was to perform an SAR study of new diphenyl PFI-3 analogs. Methods: New structural analogs of PFI-3 were developed, synthesized, and tested for their ability to enhance TMZ-induced GBM cell death by ELISA. Results: Following on the enhanced activity of compounds 2a and 2b, new diphenyl PFI-3 analogs with specific structural adjustments were made to better understand the structural requirements to optimize function. Additionally, several new structurally different candidates (e.g., 4a, 4b, and 5) showed much better efficacy in sensitizing GBM cells to TMZ-induced GBM cell death. Conclusions: Four series of PFI-3 analogs (2, 3, 4, and 5) were designed, synthesized, and tested for the ability to sensitize GBM cells to TMZ-induced cell death. Series 2 optimized the A-ring and R-isomer chirality. Series 3 used a 5-membered linker with weak activity. Series 4’s di-phenyl urea compounds showed better bromodomain inhibition. Series 5’s methoxyphenyl-B-ring analogs were exceptionally strong inhibitors.

Keywords: bromodomain ; glioblastoma (GBM) ; therapeutic enhancing drug (TED) ; anti-GBM activity ; structure-activity relationship (SAR) ; PFI-3 analog ; temozolomide (TMZ)

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Product Details of [ 60811-24-7 ]

CAS No. :60811-24-7
Formula : C6H4F2S
M.W : 146.16
SMILES Code : SC1=CC=C(F)C(F)=C1
MDL No. :MFCD03094279
InChI Key :BGVRHDQMTMPAEZ-UHFFFAOYSA-N
Pubchem ID :2778378

Safety of [ 60811-24-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
Class:3
UN#:1993
Packing Group:

Application In Synthesis of [ 60811-24-7 ]

* 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 [ 60811-24-7 ]

[ 60811-24-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 940890-90-4 ]
  • [ 60811-24-7 ]
  • C16H21F2NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.26 g With potassium carbonate; In acetonitrile;Reflux; S15 (3.63 g, 13.00 mmol) and S16 (1.58 g, 10.84 mmol) were dissolved in 50 mL of acetonitrile then K2C03 (2.39g, 17.34 mmol) was added and the reaction was refluxed. After overnight, the reaction was cooled, water was added and the solution was extracted three times with ethyl acetate. After column purification, 3.26 g of S 17 was obtained.
  • 2
  • [ 940890-90-4 ]
  • [ 60811-24-7 ]
  • tert-butyl (R)-3-((3,4-difluorophenyl)sulfonyl)piperidine-1-carboxylate [ No CAS ]
 

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