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[ CAS No. 42074-68-0 ] {[proInfo.proName]}

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Chemical Structure| 42074-68-0
Chemical Structure| 42074-68-0
Structure of 42074-68-0 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Johan Storm J?rgensen ; Elnaz Harifi Mood ; Anne Sofie Holst Knap , et al. DOI:

Abstract: In view of the increased prevalence of antimicrobial resistance among human pathogens, antibiotics against multidrug-resistant (MDR) bacteria are in urgent demand. In particular, the rapidly emerging resistance to last-resort antibiotic colistin, used for severe Gram-negative MDR infections, is critical. Here, a series of polymyxins containing unnatural were explored, and some analogues exhibited excellent activity against Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, and Pseudomonas aeruginosa. Hydrophobicity of the compounds within this series (as measured by retention in reversed-phase analytical HPLC) exhibited a discernible correlation with their antimicrobial activity. This trend was particularly pronounced for colistin-resistant pathogens. The most active compounds demonstrated competitive activity against a panel of Gram-negative pathogens, while exhibiting low in vitro cytotoxicity. Importantly, most of these hits also retained (or even had increased) potency against colistin-susceptible strains. These findings infer that fine-tuning hydrophobicity may enable the design of polymyxin analogues with favorable activity profiles.

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Product Details of [ 42074-68-0 ]

CAS No. :42074-68-0 MDL No. :MFCD00040399
Formula : C19H14Cl2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :JFLSOKIMYBSASW-UHFFFAOYSA-N
M.W : 313.22 Pubchem ID :94524
Synonyms :
Chemical Name :(Chloro(2-chlorophenyl)methylene)dibenzene

Calculated chemistry of [ 42074-68-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.05
Num. rotatable bonds : 3
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 90.07
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.24
Log Po/w (XLOGP3) : 6.21
Log Po/w (WLOGP) : 5.76
Log Po/w (MLOGP) : 6.12
Log Po/w (SILICOS-IT) : 6.14
Consensus Log Po/w : 5.49

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.13
Solubility : 0.000232 mg/ml ; 0.00000074 mol/l
Class : Poorly soluble
Log S (Ali) : -6.0
Solubility : 0.000317 mg/ml ; 0.00000101 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.69
Solubility : 0.000000634 mg/ml ; 0.000000002 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.55

Safety of [ 42074-68-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H290-H314 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 42074-68-0 ]

* 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 [ 42074-68-0 ]

[ 42074-68-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 2979-22-8 ]
  • [ 42074-68-0 ]
  • [ 196814-73-0 ]
  • (S)-2-(2-Benzoyl-phenylamino)-3-[4-(2-methoxy-2-phenyl-ethoxy)-phenyl]-propionic acid [ No CAS ]
  • 2
  • [ 42074-68-0 ]
  • [ 35661-51-9 ]
  • C19H14Cl2*C15H14N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃; 2-Chlorotrityl chloride resin (loading=0.6 mmol/g) (1 g) wasswelled in CH2Cl2/N,N-dimethylformamide (DMF)(10 mL/10 mL) at 0 °C. Fmoc-NH2NH2 (1.5 g, 10 eq.) andDIPEA (2 mL, 20 eq.) were added. The reaction was carriedout from 0 °C to r.t. overnight. Methanol (1 mL) was addedto quench the remaining 2-CTC resin. Then the resin waswashed with DMF, methanol and stored at 4 °C.
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