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[ CAS No. 25952-53-8 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Excepted Quantity USD 0.00
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Chemical Structure| 25952-53-8
Chemical Structure| 25952-53-8
Structure of 25952-53-8 * Storage: {[proInfo.prStorage]}
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Product Citations

Berg, Kaja ; Hegde, Pooja ; Pujari, Venugopal , et al. DOI: PubMed ID:

Abstract: The electron transport chain (ETC) in the cell membrane consists of a series of redox complexes that transfer electrons from electron donors to acceptors and couples this electron transfer with the transfer of protons (H+) across a membrane. This process generates proton motive force which is used to produce ATP and a myriad of other functions and is essential for the long-term survival of Mycobacterium tuberculosis (Mtb), the causative organism of tuberculosis (TB), under the hypoxic conditions present within infected granulomas. Menaquinone (MK), an important carrier molecule within the mycobacterial ETC, is synthesized de novo by a cluster of enzymes known as the classic/canonical MK biosynthetic pathway. MenA (1,4-dihydroxy-2-naphthoate prenyltransferase), the antepenultimate enzyme in this pathway, is a verified target for TB therapy. In this study, we explored structure-activity relationships of a previously discovered MenA inhibitor scaffold, seeking to improve potency and drug disposition properties. Focusing our campaign upon three molecular regions, we identified two novel inhibitors with potent activity against MenA and Mtb (IC50 = 13-22 μM, GIC50 = 8-10 μM). These analogs also displayed substantially improved pharmacokinetic parameters and potent synergy with other ETC-targeting agents, achieving nearly complete sterilization of Mtb in combination therapy within two weeks in vivo. These new inhibitors of MK biosynthesis present a promising new strategy to curb the continued spread of TB.

Keywords: 1,4-dihydroxy-2-naphthoate prenyltransferase ; MenA ; MenA inhibitors ; Menaquinone ; Mtb ; Mycobacterium tuberculosis ; Piperidine derivatives ; SAR

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Product Details of [ 25952-53-8 ]

CAS No. :25952-53-8 MDL No. :MFCD00012503
Formula : C8H18ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :FPQQSJJWHUJYPU-UHFFFAOYSA-N
M.W : 191.70 Pubchem ID :2723939
Synonyms :

Calculated chemistry of [ 25952-53-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.88
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.49
TPSA : 27.96 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.67
Log Po/w (WLOGP) : 1.93
Log Po/w (MLOGP) : 1.29
Log Po/w (SILICOS-IT) : 1.72
Consensus Log Po/w : 1.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.38
Solubility : 0.798 mg/ml ; 0.00416 mol/l
Class : Soluble
Log S (Ali) : -2.91
Solubility : 0.236 mg/ml ; 0.00123 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.12
Solubility : 1.45 mg/ml ; 0.00759 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 25952-53-8 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P260-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352+P312-P314-P333+P313-P391-P405-P501 UN#:2811
Hazard Statements:H302-H311-H315-H317-H373-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 25952-53-8 ]

* 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 [ 25952-53-8 ]
  • Downstream synthetic route of [ 25952-53-8 ]

[ 25952-53-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 25952-53-8 ]
  • [ 1892-57-5 ]
Reference: [1] Patent: US2007/197576, 2007, A1, . Location in patent: Page/Page column 4
  • 2
  • [ 628-13-7 ]
  • [ 1892-57-5 ]
  • [ 25952-53-8 ]
YieldReaction ConditionsOperation in experiment
71.2 g at 30℃; Weigh 24ml of carbon disulfide dissolved in 150ml methanol,43.8 g of N, N'-dimethylpropylenediamine was slowly added dropwise to control the temperature at 10-15 ° C,The dropwise addition process was carried out with a white solid which was added dropwise at 20 ° C for 2 hours, filtered and washed with methanol to give 75 g of a white solid (Intermediate 1) in 96percent yield.75 g of the product was weighed, 200 ml of dichloromethane was added, and the temperature was controlled at 10-15 ° C. 45.8 g of triethylamine was added, followed by slowly dropping 50.3 g of ethyl chloroformate, dropping for 2 hours,After the dropwise addition was carried out for 1 hour, the organic phase was washed, washed, filtered and dried to give the product (Intermediate 2).25.2 g of ethylamine (containing 70percent water) was weighed, 180 ml of dichloromethane was added,Cooling to 10-15 ° C, slowly dropping intermediate 2, dropping finish for 1 hour,The organic phase was washed with an alkali of pH 11-12, dried, under reduced pressure, and concentrated to give 90 g of an oil, (Intermediate 3)0.02 g of EDTA was added and oxidized at 30 ° C with 630 g of sodium hypochlorite at a mass concentration of 10percent. After completion of the oxidation,Extraction layer, the organic phase after drying and vacuum concentration 30 , the solvent evaporated, the vacuum distillation to get EDC,Purity 99.4percent;41.4 g of pyridine hydrochloride was weighed, 120 ml of dichloromethane was added, and the mixture was heated at 30 ° C,Slowly dropping the distillation of the EDC, first dissolved, and then precipitation of crystals, dripping finished, cooling to 5 ,Crystallization 1h, filtration, to be 71.2g EDC hydrochloride, purity 99.5percentYield 81percent (based on N, N'-dimethylpropylenediamine).
Reference: [1] Patent: CN104193654, 2016, B, . Location in patent: Paragraph 0055
  • 3
  • [ 18997-72-3 ]
  • [ 25952-53-8 ]
Reference: [1] Patent: CN104193654, 2016, B,
  • 4
  • [ 27421-70-1 ]
  • [ 25952-53-8 ]
Reference: [1] Patent: CN104193654, 2016, B,
  • 5
  • [ 109-55-7 ]
  • [ 25952-53-8 ]
Reference: [1] Patent: CN104193654, 2016, B,
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