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[ CAS No. 611-98-3 ] {[proInfo.proName]}

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Chemical Structure| 611-98-3
Chemical Structure| 611-98-3
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Quality Control of [ 611-98-3 ]

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Product Citations

Product Citations

Werman, Joshua M. ; Chen, Yu-Ching ; Yuan, Tianao , et al. DOI: PubMed ID:

Abstract: By illuminating key 6-azasteroid-protein interactions in both Mycobacterium tuberculosis (Mtb) and the closely related model organism Mycobacterium marinum (Mm), we sought to improve the antimycobacterial potency of 6-azasteroids and further our understanding of the mechanisms responsible for their potentiation of the antituberculosis drug bedaquiline. We selected a newly developed 6-azasteroid analog and an analog reported previously (ACS Infect. Dis.2019, 5 (7), 1239-1251) to study their phenotypic effects on Mtb and Mm, both alone and in combination with bedaquiline. The 6-azasteroid analog, 17β-[N-(4-trifluoromethoxy-diphenylmethyl)carbamoyl]-6-propyl-azaandrostan-3-one, robustly potentiated bedaquiline-mediated antimycobacterial activity, with a nearly 8-fold reduction in Mm bedaquiline minimal inhibitory concentration (85 nM alone vs. 11 nM with 20 μM 6-azasteroid). This analog displayed minimal inhibitory activity against recombinant mycobacterial 3β-hydroxysteroid dehydrogenase, a previously identified target of several 6-azasteroids. Dose-dependent potentiation of bedaquiline by this analog reduced mycobacterial intracellular ATP levels and impeded the ability of Mtb to neutralize exogenous oxidative stress in culture. We developed two 6-azasteroid photoaffinity probes to investigate azasteroid-protein interactions in Mm whole cells. Using bottom-up mass spectrometric profiling of the cross-linked proteins, we identified eight potential Mm/Mtb protein targets for 6-azasteroids. The nature of these potential targets indicates that proteins related to oxidative stress resistance play a key role in the BDQ-potentiating activity of azasteroids and highlights the potential impact of inhibition of these targets on the generation of drug sensitivity.

Keywords: photoaffinity label ; click chemistry ; synergy ; potentiator ; oxidative stress ; inhibitor

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Product Details of [ 611-98-3 ]

CAS No. :611-98-3 MDL No. :MFCD00038138
Formula : C13H12N2O Boiling Point : No data available
Linear Structure Formula :H2NC6H4COC6H4NH2 InChI Key :ZLSMCQSGRWNEGX-UHFFFAOYSA-N
M.W : 212.25 Pubchem ID :69149
Synonyms :
Chemical Name :Bis(4-aminophenyl)methanone

Calculated chemistry of [ 611-98-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 65.13
TPSA : 69.11 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 2.26
Log Po/w (WLOGP) : 2.1
Log Po/w (MLOGP) : 1.73
Log Po/w (SILICOS-IT) : 1.94
Consensus Log Po/w : 1.89

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.0
Solubility : 0.211 mg/ml ; 0.000994 mol/l
Class : Soluble
Log S (Ali) : -3.35
Solubility : 0.0953 mg/ml ; 0.000449 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.15
Solubility : 0.015 mg/ml ; 0.0000705 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 611-98-3 ]

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

Application In Synthesis of [ 611-98-3 ]

* 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 [ 611-98-3 ]

[ 611-98-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 611-98-3 ]
  • [ 134521-16-7 ]
  • 2
  • [ 2719-05-3 ]
  • [ 611-98-3 ]
  • 3
  • [ 548-62-9 ]
  • N,N',N''-trimethylpararosaniline [ No CAS ]
  • N,N'-dimethylpararosaniline [ No CAS ]
  • [ 150-75-4 ]
  • [ 81260-56-2 ]
  • [ 619-60-3 ]
  • [ 611-98-3 ]
  • [ 3708-39-2 ]
  • C22H24N3(1+)*Cl(1-) [ No CAS ]
  • C21H22N3(1+)*Cl(1-) [ No CAS ]
  • C20H20N3(1+)*Cl(1-) [ No CAS ]
  • C23H26N3(1+)*Cl(1-) [ No CAS ]
  • [ 81260-55-1 ]
  • [ 123-30-8 ]
  • [ 71143-08-3 ]
  • [ 569-61-9 ]
  • crystal violet chloride [ No CAS ]
  • [ 90-94-8 ]
  • [ 5809-25-6 ]
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Technical Information

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