1206524-85-7|8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylic acid, 5-(1,1-dimethylethyl)-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-14-methoxy-3,6-dioxo-, (1ar,5s,8s,10r,22ar)-| Ambeed

Structure of MK-5172
CAS No.: 1206524-85-7

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Quality Control of [ 1206524-85-7 ] Purity: 99% SDS Specification

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Product Details of [ 1206524-85-7 ]

CAS No. :	1206524-85-7
Formula :	C₂₉H₃₈N₄O₇
M.W :	554.63
SMILES Code :	O=C([C@H]1N(C2)C([C@H](C(C)(C)C)NC(O[C@@]3([H])[C@](C3)([H])CCCCCC4=NC5=CC=C(OC)C=C5N=C4O[C@]2([H])C1)=O)=O)O
MDL No. :	MFCD31561044
InChI Key :	IVROMYPOGKZNLP-FDOFPDFBSA-N
Pubchem ID :	46930991

Safety of [ 1206524-85-7 ]

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

Computational Chemistry of [ 1206524-85-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	40
Num. arom. heavy atoms	10
Fraction Csp3	0.62
Num. rotatable bonds	3
Num. H-bond acceptors	9.0
Num. H-bond donors	2.0
Molar Refractivity	154.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	140.18 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.97
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	4.64
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.96
Log P_o/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.	1.79
Log P_o/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	1.95
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.06

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-6.19
Solubility	0.000359 mg/ml ; 0.000000647 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-7.31
Solubility	0.0000272 mg/ml ; 0.000000049 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
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	-5.46
Solubility	0.00195 mg/ml ; 0.00000351 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
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.	-6.39 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	1.0
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	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

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	0.0 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<2.0
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)	6.9

Application In Synthesis of [ 1206524-85-7 ]

* 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.

Downstream synthetic route of [ 1206524-85-7 ]

[ 1206524-85-7 ] Synthesis Path-Downstream 1~35

1
(1R,2S)-1-amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide hydrochloride [ No CAS ]
[ 1206524-85-7 ]
[ 1350514-68-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h;	A solution (0.1 M) of <strong>[1206524-85-7](1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylic acid</strong> in CH2Cl2 was treated with (1R,2S)-1-[(cyclopropylsulfonyl)amino]carbonyl}-2-vinylcyclopropanaminium chloride (1.3 eq), DIEA (3 eq), DMAP (1.5 eq) and TBTU (1.45 eq). The resulting mixture was stirred at 20 C. for 18 h and then diluted with EtOAc. The solution was washed with aqueous HCl (0.2 M), saturated aqueous NaHCO3 and brine. The organic phases were dried and concentrated to give a residue that was purified by flash-chromatography (eluent 2.5% MeOH/CH2Cl2) to give the title compound (89%) as a solid. 13C NMR (100 MHz, DMSO-d6) delta 172.32, 170.63, 169.04, 159.86, 156.95, 154.74, 148.10, 140.41, 133.55 (2 signals), 128.94, 118.21, 117.58, 105.89, 74.88, 59.75, 58.71, 55.68, 54.13, 54.01, 40.13, 34.49, 34.04, 33.76, 32.68, 30.71, 30.43, 28.55, 27.69, 27.28, 26.38, 21.98, 18.49, 10.67, 5.69, 5.46; MS (ES+) m/z 767 (M+H)+

References: [1]Patent: US2010/29666,2010,A1 .Location in patent: Page/Page column 10.
[2]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 332 - 336.

2
[ 1206524-84-6 ]
[ 1206524-85-7 ]

Yield	Reaction Conditions	Operation in experiment
98%		A solution (0.1 M) of methyl (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylate in a 1:1 mixture of H2O/THF was treated with LiOH.H2O (3 eq). The resulting mixture was stirred at 20 C. for 18 h, acidified with aqueous HCl (0.2 M) and diluted with EtOAc. The organic phase was separated, washed with aqueous HCl (0.2 M) and brine then dried. Removal of the volatiles afforded the title compound (98%) as a solid. MS (ES+) m/z 555 (M+H)+
	With sodium hydroxide; In methanol; at 50℃;	To a slurry of macrocyclic ester 18 (90 g, 158.3 mmol) in MeOH (720 mL) at ambient temperature was added 2 M NaOH (237.4 mL, 475 mmol) dropwise. The reaction mixture was aged at 50 C for 2-3 hours. The reaction solution was cooled to 35-00 C and 5 N HCl in 50% aq MeOH (70 mL) was added dropwise. The batch was seeded with free acid hemihydrate 19 (-100 mg) and aged for 30 min to 1 hour at 40 C. Additional 5 N HCl in 50% aq MeOH (30 mL) was added dropwise over 2-4 hours at 40 C. The slurry was aged additional 1 hour before cooling to ambient temperature. The slurry was aged for additional 1 hour before filtration. The wet cake was washed with 65% MeOH in water (3x 270 mL, displacement wash, slurry wash and displacement wash). Suction dry at ambient temperature or vacuum oven dry with dry N2 sweep at 60-80 C gave 85.6 g of macrocyclic acid hemihydrate 19 as an off- white solid. 'H NMR (400 MHz, CDCl3) delta 7.85 (d, J = 9.0 Hz, 1 H), 7.19 (dd, J = 9.0, 2.8 Hz, 1 H), 7.13 (d, J = 2.8 Hz, 1 H), 5.99 (t, J = 3.9 Hz, 1 H), 5.45 (d, J = 9.9 Hz, 1 H), 4.80 (s, br, 2 H, COOH, hemihydrate H2O), 4.64 (dd, J = 10.4, 7.4 Hz, 1 H), 4.49 (d, J = 11.6 Hz, 1 H), 4.44 (d, J= 10.0 Hz, 1 H), 3.99 (dd, J = 11.7, 4.0 Hz, 1 H), 3.94 (s, 3 H), 3.81 (m, 1 H), 2.90 (ddd, J = 13.8, 11.8, 4.8, 1 H), 2.80 (ddd, J = 13.8, 11.8, 4.8 Hz, 1 H), 2.71 (dd, J = 14.3, 7.3, 1 H), 2.42 (ddd, J = 14.4, 10.6, 4.2 Hz, 1 H), 1.76 (m, 2 H), 1.66 (m, 2 H), 1.52 (m, 3 H), 1.07 (s, 9 H), 0.96 (m, 2 H), 0.67 (m, 1 H), 0.47 (m, I H). 13C NMR (100 MHz, CDCl3) delta 174.5, 172.1, 160.5, 157.6, 155.1, 148.6, 141.0, 134.3, 129.1, 118.9, 106.1, 74.3, 59.6, 58.3, 55.6, 54.6, 35.6, 35.3, 33.7, 30.8, 29.4, 28.6, 283, 26.5, 18.9, 11.2. IPC HPLC conditions: Hypersil Gold PFP Column, 150 x 4.6mm, 3.0mum, Column temperature of 40 C; Flow rate of 1.8 mL/min; and Wavelength of 215 nm

References: [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 332 - 336.
[2]Patent: US2010/29666,2010,A1 .Location in patent: Page/Page column 10.
[3]Organic Letters,2013,vol. 15,p. 4174 - 4177.
[4]Organic Letters,2018,vol. 20,p. 7261 - 7265.
[5]Patent: EP2764866,2014,A1 .Location in patent: Paragraph 0188.
[6]Patent: WO2015/57611,2015,A1 .Location in patent: Page/Page column 44-45.

3
[ 1206524-85-7 ]
potassium [(1R,2S)-1-([(1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxalin-8-yl]carbonyl}amino)-2-ethenylcyclopropyl]carbonyl}(cyclopropylsulfonyl)azanide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 332 - 336.
[2]Patent: EP2764866,2014,A1 .

4
[ 1206524-79-9 ]
[ 1206524-85-7 ]

References: [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 332 - 336.
[2]Organic Letters,2013,vol. 15,p. 4174 - 4177.
[3]Patent: EP2764866,2014,A1 .
[4]Patent: EP2764866,2014,A1 .
[5]Patent: WO2015/57611,2015,A1 .
[6]Organic Letters,2018,vol. 20,p. 7261 - 7265.
[7]Organic Letters,2018,vol. 20,p. 7261 - 7265.
[8]Organic Letters,2018,vol. 20,p. 7261 - 7265.

5
1-(tert-butyl) 2-methyl (2S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylate [ No CAS ]
[ 1206524-85-7 ]