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[ CAS No. 67-36-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 67-36-7
Chemical Structure| 67-36-7
Chemical Structure| 67-36-7
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Product Citations

Product Citations

Christian N. Lotz ; Alina Krollenbrock ; Lea Imhof , et al. DOI:

Abstract: Schistosomiasis caused by Schistosoma spp. is a disease that causes a considerable health burden to millions of people worldwide. The limited availability of effective drugs on the market and the increased risk of resistance development due to extensive usage, highlight the urgent need for new antischistosomal drugs. Recent studies have shown that robenidine derivatives, containing an aminoguanidine core, exhibit promising activities against Plasmodium falciparum, motivating further investigation into their efficacy against Schistosoma mansoni, due to their similar habitat and the resulting related cellular mechanisms like the heme detoxification pathway. The conducted phenotypic screening of robenidine and 80 derivatives against newly transformed schistosomula and adult Schistosoma mansoni yielded 11 candidates with low EC50 values for newly transformed schistosomula (1.12–4.63 μM) and adults (2.78–9.47 μM). The structure-activity relationship revealed that electron-withdrawing groups at the phenyl moiety, as well as the presence of methyl groups adjacent to the guanidine moiety, enhanced the activity of derivatives against both stages of Schistosoma mansoni. The two compounds 2,2′-Bis[(3-cyano-4-fluorophenyl)methylene] carbonimidic Dihydrazide Hydrochloride (1) and 2,2′-Bis[(4-difluoromethoxyphenyl) ethylidene] carbonimidic Dihydrazide Hydrochloride (19), were selected for an in vivo study in Schistosoma mansoni-infected mice based on their potency, cytotoxicity, pharmacokinetic-, and physicochemical properties, but failed to reduce the worm burden significantly (worm burden reduction <20%). Thus, robenidine derivatives require further refinements to obtain higher antischistosomal specificity and in vivo activity.

Keywords: Robenidine derivative ; Aminoguanidine ; Schistosoma mansoni ; Drug discovery ; Structure-activity relationship

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Product Details of [ 67-36-7 ]

CAS No. :67-36-7 MDL No. :MFCD00003383
Formula : C13H10O2 Boiling Point : -
Linear Structure Formula :OCH(C6H4)O(C6H5) InChI Key :QWLHJVDRPZNVBS-UHFFFAOYSA-N
M.W : 198.22 Pubchem ID :66139
Synonyms :

Calculated chemistry of [ 67-36-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.35
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 3.07
Log Po/w (WLOGP) : 3.29
Log Po/w (MLOGP) : 2.61
Log Po/w (SILICOS-IT) : 3.22
Consensus Log Po/w : 2.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.4
Solubility : 0.0795 mg/ml ; 0.000401 mol/l
Class : Soluble
Log S (Ali) : -3.29
Solubility : 0.102 mg/ml ; 0.000514 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.61
Solubility : 0.00489 mg/ml ; 0.0000247 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.36

Safety of [ 67-36-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 67-36-7 ]

* 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.

  • Upstream synthesis route of [ 67-36-7 ]
  • Downstream synthetic route of [ 67-36-7 ]

[ 67-36-7 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 67-36-7 ]
  • [ 1779-49-3 ]
  • [ 4973-29-9 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 35, p. 4473 - 4476
[2] Organic Letters, 2016, vol. 18, # 24, p. 6428 - 6431
[3] Patent: US5783593, 1998, A,
[4] Patent: WO2010/135360, 2010, A1, . Location in patent: Page/Page column 174; 208
  • 2
  • [ 67-36-7 ]
  • [ 4973-29-9 ]
Reference: [1] Patent: US5631401, 1997, A,
  • 3
  • [ 67-36-7 ]
  • [ 19493-09-5 ]
  • [ 4973-29-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 18, p. 3190 - 3194
  • 4
  • [ 67-36-7 ]
  • [ 107622-80-0 ]
YieldReaction ConditionsOperation in experiment
75% With hydroxylamine hydrochloride In ethanol; water at 20℃; Inert atmosphere A solution of 4-phenoxybenzaldehyde (2.0 g, 10 mmol), hydroxylamine hydrochloride (700 mg, 10 mmol), EtOH (20 ml), and water (1 ml) was stirred at room temperature overnight. To the reaction mixture were added 10 N Hci (1 ml) and of Pd/C (10percent on carbon, 320 mg) and was stirred under hydrogen for 30 min. The reaction mixture was filtrated through Celite and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound as a white solid (1.5 g, 75percent yield).
75%
Stage #1: With hydroxylamine hydrochloride In ethanol; water at 20℃;
Stage #2: With hydrogenchloride; palladium 10% on activated carbon; hydrogen In ethanol; water for 0.5 h;
A solution of 4-phenoxybenzaldehyde (2.0 g, 10 mmol), hydroxylamine hydrochloride (700 mg, 10 mmol), EtOH (20 ml), and water (1 ml) was stirred at room temperature overnight. To the reaction mixture were added 10 N HCl (1 ml) and of Pd/C (10percenton carbon, 320 mg) and was stirred under hydrogen for 30 min. The reaction mixture was filtrated through Celite and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound as a white solid (1.5 g, 75percent yield).
Reference: [1] Patent: WO2017/100668, 2017, A1, . Location in patent: Page/Page column 164
[2] Patent: WO2018/103058, 2018, A1, . Location in patent: Page/Page column 164
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