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Chemical Structure| 72235-53-1 Chemical Structure| 72235-53-1

Structure of 72235-53-1

Chemical Structure| 72235-53-1

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Product Citations

Product Citations

Dube, Phelelisiwe S. ; Legoabe, Lesetja J. ; Jordaan, Audrey ; Sigauke, Lester ; Warner, Digby F. ; Beteck, Richard M.

Abstract: Mycobacterium tuberculosis (Mtb) has an impermeable cell wall which gives it an inherent ability to resist many antibiotics. DprE1, an essential enzyme in Mtb cell wall synthesis, has been validated as a target for several TB drug candidates. The most potent and developmentally advanced DprE1 inhibitor, PBTZ169, is still undergoing clin. development. With high attrition rate, there is need to populate the development pipeline. Using a scaffold hopping strategy, we imprinted the benzenoid ring of PBTZ169 onto a quinolone nucleus. Twenty-two compounds were synthesized and screened for activity against Mtb, with six compounds exhibiting sub micromolar activity of MIC90 <0.244 μM. Compound 25 further demonstrated sub-micromolar activity when evaluated against wild-type and fluoroquinolone-resistant Mtb strains. This compound maintained its sub-micromolar activity against a DprE1 P116S mutant strain but showed a significant reduction in activity when tested against the DprE1 C387S mutant.

Keywords: DprE1 ; Quinolone ; Nitro compounds ; Mycobacterium tuberculosis ; Benzothiazinone

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Product Details of [ 72235-53-1 ]

CAS No. :72235-53-1
Formula : C7H7F2N
M.W : 143.13
SMILES Code : NCC1=CC(F)=C(F)C=C1
MDL No. :MFCD00010145
InChI Key :PHLZUDXEBCQHKM-UHFFFAOYSA-N
Pubchem ID :123572

Safety of [ 72235-53-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:2735
Packing Group:

Application In Synthesis of [ 72235-53-1 ]

* 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 [ 72235-53-1 ]

[ 72235-53-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 369-26-6 ]
  • [ 72235-53-1 ]
  • [ 1305089-87-5 ]
YieldReaction ConditionsOperation in experiment
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; In tetrahydrofuran; at 80℃; Step 1 : 3-Amino-N-(3,4-difluorobenzyl)-4-fluorobenzamideA mixture comprising <strong>[369-26-6]methyl 3-amino-4-fluorobenzoate</strong> (2 g, 1 1.82 mmol), (3,4- difluorophenyl)methanamine (2.54 g, 17.74 mmol) and TBD (1 .646 g, 1 1.82 mmol) in THF (39.4 ml) was heated at 80°C overnight. After cooling to RT, the mixture was purified by chromatography on silica eluting with 0-20percent 2M NH3 in MeOH/DCM to afford the title compound.
 

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