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Chemical Structure| 15529-49-4 Chemical Structure| 15529-49-4

Structure of 15529-49-4

Chemical Structure| 15529-49-4

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Product Citations

Product Citations

White, Robert H. ; Allen, Kylie D. ; Wegener, Gunter ;

Abstract: The anaerobic oxidation of methane (AOM) mitigates the flux of methane from marine sediments into the water column. AOM is performed by anaerobic methanotrophic archaea (ANME) that reverse the methanogenesis pathway and partner bacteria that utilize the released reducing equivalent for sulfate reduction We investigated small-mol. extracts from sediment-free thermophilic enrichment cultures of ANME-1 and sulfate-reducing bacteria using ultraperformance liquid chromatog. with high-resolution mass spectrometry. During the anal., we discovered a novel thioquinoxalinol-containing redox mol. as a major component of the chem. derivatized small-mol. pool. This compound contains both a redox active quinoxaline heterocyclic ring and a thiol group. Addnl., the same structure was identified that contains a sulfate ester on the hydroxyl group, which likely makes the mol. more water soluble Hydrated versions of both structures were also observed as major compounds in the extracts On the basis of reactions of model compounds such as quinoxalin-6-ol, the hydrated version appears to be formed from the addition of water to the dehydropyrazine ring followed by an oxidation These thioquinoxalinol compounds, which represent completely new structures in biochem., may be involved in electron transport processes within and(or) between ANME-1 and sulfate-reducing bacteria, may serve protective roles by reacting with toxic compounds such as hydrogen sulfide, or may transport sulfate as a sulfate ester into the sulfate-reducing bacteria.

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Alternative Products

Product Details of [ 15529-49-4 ]

CAS No. :15529-49-4
Formula : C54H45Cl2P3Ru
M.W : 958.83
SMILES Code : [Cl-][Ru+2]([Cl-])([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)[P](C7=CC=CC=C7)(C8=CC=CC=C8)C9=CC=CC=C9
MDL No. :MFCD00013077
InChI Key :WIWBLJMBLGWSIN-UHFFFAOYSA-L
Pubchem ID :11007548

Safety of [ 15529-49-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 15529-49-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 60
Num. arom. heavy atoms 54
Fraction Csp3 0.0
Num. rotatable bonds 12
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 267.15
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

40.77 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

15.43
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

4.34
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

10.86
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

11.49
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

8.42

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-15.38
Solubility 0.0 mg/ml ; 4.17e-16 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Insoluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-16.42
Solubility 0.0 mg/ml ; 3.81e-17 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Insoluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-23.6
Solubility 2.41e-21 mg/ml ; 2.51e-24 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Insoluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-1.19 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

2.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

1.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

3.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.17

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<3.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

7.8

Application In Synthesis of [ 15529-49-4 ]

* 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 [ 15529-49-4 ]

[ 15529-49-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 15529-49-4 ]
  • [ 17217-57-1 ]
  • [ 366452-46-2 ]
YieldReaction ConditionsOperation in experiment
Ca. 78 mg In dichloromethane; at 20℃; for 0.5h; General procedure: All the solvents used in this work were of reagent quality and usedwithout further purification. Lapachol was obtained according to theprocedure described in [24]. The precursors cis-[RuCl2(PPh3)2(X-bipy)](X = H, methyl (Me) and methoxy (MeO)) and cis-[RuCl2(PPh3)2(phen)] were prepared according to literature [26,27]. Typically[100.0 mg; 0.1 mmol] of the [RuCl2(PPh3)3] was dissolved in degassed20 mL of dichloromethane (Merck) and N-heterocyclic (X-bipy or phen) [22.0 mg; 0.11 mmol] ligand was added. The reaction mixturewas stirred for 30 min at room temperature and the volume of theresulting blue solution was reduced, under vacuum, to ca. 2 mL anddiethyl ether (Merck) was then added to precipitate a red solid, whichwas filtered off, washed several times with diethyl ether, and driedunder vacuum. Yield: ~78 mg (80?90percent).
  • 2
  • [ 15529-49-4 ]
  • [ 34272-64-5 ]
  • [ruthenium(II)chloride(triphenylphosphine)3(2-mercapto-4-methyl-5-thiadiazolacetic acide(-H))] [ No CAS ]
  • 3
  • [ 15529-49-4 ]
  • [ 2530-85-0 ]
  • [RuCl22-O,O-O2CC=CH2(CH3)}(PPh3)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% 2-Methyl-acrylic acid 3-trimethoxysilane propyl ester (87 mg, 0.35 mmol) in dry THF was treated with triethylamine (0.20 mL) and the mixture was stirred for 30 min at ambient temperature under air. [RuCl2(PPh3)3] (335 mg, 0.35 mmol) was added and the reaction mixture was stirred at reflux for 2 h, during which there was a color residue was washed with diethyl ether and hexane. Recrystallization from CH2Cl2/hexane afforded dark green crystals of 1 in a week. Yield: 128 mg, 47% (based on Ru). IR (KBr disc, cm-1): nu(C=C) 1623 (s), nu(OCO) 1504 (s) and 1472 (s). MS (FAB): m/z = 781 [M]+, 746 [M-Cl]+, 711 [M-2Cl]+. mueff = 1.93 muB. Anal. for C40H35O2Cl2P2Ru: calcd. C 61.46, H 4.51%; found C 61.41, H 4.48%.
  • 4
  • [ 15529-49-4 ]
  • [ 69605-90-9 ]
  • 2-(dicyclohexylphosphanyl)aniline [ No CAS ]
  • [ 7688-25-7 ]
  • C59H65ClNP3Ru [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With triethylamine; In toluene; at 110℃; for 18h;Inert atmosphere; A 50 ml three-necked flask equipped with a stirring reflux device was charged with 1 mmol of 2-dicyclohexylphosphine aniline,1.6 mmol of m-phenylbenzyl alcohol, 1 mmol of bis-diphenylphosphine butane, 1 mmol of RuCl2 (PPh3) 3, 1 mmol of triethylamine and 20 ml of toluene were added and the mixture was heated at 110 C. for 18 h under a nitrogen atmosphere.After cooling and filtering, the resulting solid was recrystallized from a mixed solvent of CH 2 Cl 2 and petroleum ether to give product 10 in a yield of 84%.
  • 5
  • [ 15529-49-4 ]
  • [ 612-16-8 ]
  • 2-diethylphosphinoaniline [ No CAS ]
  • [ 434336-16-0 ]
  • C54H75ClNO2P3Ru [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With potassium hydroxide; In benzene; at 100℃; for 18h;Inert atmosphere; A 50 ml three-necked flask equipped with a stirring reflux device was charged with 1 mmol of 2-diethylphosphine aniline,1.3 mmol of o-methoxybenzyl alcohol, 1 mmol2-dicyclohexylphosphine oxide, 1 mmol RuCl2 (PPh3) 3, 1.1 mmol potassium hydroxide, 20 ml benzene and heating at a temperature of 100 C for 18 h under a nitrogen atmosphere,After cooling and filtering, the resulting solid was recrystallized from a mixed solvent of CH 2 Cl 2 and petroleum ether to give product 15 in a yield of 80%.
  • 6
  • [ 15529-49-4 ]
  • [ 17217-57-1 ]
  • C15H19Ag2N5(2+)*2Cl(1-) [ No CAS ]
  • C27H29ClN7O2Ru(1+) [ No CAS ]
 

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