[ CAS No. 163042-96-4 ] {[proInfo.proName]}

Name: 163042-96-4|(2S,3S,4R,5R)-5-(2-Chloro-6-((3-iodobenzyl)amino)-9H-purin-9-yl)-3,4-dihydroxy-N-methyltetrahydrofuran-2-carboxamide|99%
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SKU: A138589
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Quality Control of [ 163042-96-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 163042-96-4 ]

SDS Specification

Alternatived Products of [ 163042-96-4 ]

Product Details of [ 163042-96-4 ]

CAS No. :	163042-96-4	MDL No. :	MFCD01861178
Formula :	C₁₈H₁₈ClIN₆O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IPSYPUKKXMNCNQ-PFHKOEEOSA-N
M.W :	544.73	Pubchem ID :	3035850
Synonyms :	2-Cl-IB-MECA;CF-102;Chloro-IB-MECA;Cl-IB-MECA;2-Chloro-IB-MECA	Chemical Name :	(2S,3S,4R,5R)-5-(2-Chloro-6-((3-iodobenzyl)amino)-9H-purin-9-yl)-3,4-dihydroxy-N-methyltetrahydrofuran-2-carboxamide

Calculated chemistry of [ 163042-96-4 ]

Physicochemical Properties

Num. heavy atoms :	30
Num. arom. heavy atoms :	15
Fraction Csp3 :	0.33
Num. rotatable bonds :	6
Num. H-bond acceptors :	7.0
Num. H-bond donors :	4.0
Molar Refractivity :	116.44
TPSA :	134.42 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-8.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.76
Log Po/w (XLOGP3) :	1.86
Log Po/w (WLOGP) :	0.39
Log Po/w (MLOGP) :	0.32
Log Po/w (SILICOS-IT) :	0.76
Consensus Log Po/w :	1.22

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.36
Solubility :	0.0236 mg/ml ; 0.0000433 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.3
Solubility :	0.027 mg/ml ; 0.0000496 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.82
Solubility :	0.00834 mg/ml ; 0.0000153 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.45

Safety of [ 163042-96-4 ]

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

Application In Synthesis of [ 163042-96-4 ]

* 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.

Upstream synthesis route of [ 163042-96-4 ]
Downstream synthetic route of [ 163042-96-4 ]

[ 163042-96-4 ] Synthesis Path-Upstream 1~11

1
[ 74-89-5 ]
[ 163042-96-4 ]

Yield	Reaction Conditions	Operation in experiment
31.8%	Stage #1: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In water; acetonitrile at 20℃; for 4 h; Stage #2: With thionyl chloride In ethanol at 0 - 20℃; for 12 h; Inert atmosphere Stage #3: at 20℃; for 12 h;	The intermediate compound (15 g, 26.89 mmol) prepared in Step 3Acetonitrile-water (130 mL, 1: 1)It was dissolved in a solution(Di acetoxy iodo) benzene(19 g, 59.16 mmol)And 2,2,6,6-tetramethyl-1-piperidinyl oxyl (840 mg, 5.37mmol) toIt was added dropwise and then stirred at room temperature for 4 hours.After confirmation of the completion of the reaction the reaction solution was concentrated under reduced pressure to give the acid intermediate, without purification.Acid intermediate thus obtained (15 g, 26.23 mmol)In absolute ethanol (500mL) in a stream of nitrogenA dissolved and then cooled to 0 thionyl chloride (9.52 mL, 131.17 mmol)It was added dropwise slowly and then stirred at room temperature for 12 hours.After confirmation of the completion of the reaction the reaction solution was concentrated under reduced pressure to give the intermediate ethyl ester without purification.This was added dropwise to the resulting ethyl ester intermediate (15.5 g, 25.84 mmol), methylamine (750 mL, 2 N THF solution) then stirred at room temperature for 12 hours.Concentrated under reduced pressure and then check the completion of the reaction, and then separating the obtained residue was purified by column chromatography to intermediate compound (2S, 5R) -5- (2- chloro-6- (3-iodo-benzylamino) -9H- purine 9-yl) -N- methyl-3,4-dihydroxy-2-carboxamide in tetrahydrofuran (5 g, to give a 31.80percent)

Reference： [1] Patent: KR2015/10195, 2015, A, . Location in patent: Paragraph 0191-0193; 0206; 0207

2
[ 163042-90-8 ]
[ 163042-96-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 21, p. 3614 - 3621

3
[ 5451-40-1 ]
[ 163042-96-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 21, p. 3614 - 3621
[2] Patent: KR2015/10195, 2015, A,

4
[ 3718-88-5 ]
[ 163042-96-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 21, p. 3614 - 3621

5
[ 120046-86-8 ]
[ 163042-96-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 21, p. 3614 - 3621

6
[ 163042-95-3 ]
[ 163042-96-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 21, p. 3614 - 3621

7
[ 6974-32-9 ]
[ 163042-96-4 ]

Reference： [1] Patent: KR2015/10195, 2015, A,

8
[ 163152-31-6 ]
[ 163042-96-4 ]

Reference： [1] Patent: KR2015/10195, 2015, A,

9
[ 15373-23-6 ]
[ 163042-96-4 ]

Reference： [1] Patent: KR2015/10195, 2015, A,

10
[ 163152-42-9 ]
[ 163042-96-4 ]

Reference： [1] Patent: KR2015/10195, 2015, A,

11
[ 152918-18-8 ]
[ 163042-96-4 ]

Reference： [1] Patent: US2005/256143, 2005, A1, . Location in patent: Page/Page column Sheet 1 of 3

[ 163042-96-4 ] Synthesis Path-Downstream 1~21

1
[ 163042-96-4 ]
[ 5188-07-8 ]
(2S,3S,4R,5R)-3,4-Dihydroxy-5-[6-(3-iodo-benzylamino)-2-methylsulfanyl-purin-9-yl]-tetrahydro-furan-2-carboxylic acid methylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3614 - 3621

2
[ 163042-90-8 ]
[ 163042-96-4 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3614 - 3621

3
[ 163042-96-4 ]
[ 74-89-5 ]
MRS 537 [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3614 - 3621

4
[ 6160-65-2 ]
[ 163042-96-4 ]
2-chloro-N⁶-(3-iodobenzyl)-9-<5-(methylcarbamoyl)-2,3-O-(thiocarbonyl)-β-D-ribofuranosyl>adenine [ No CAS ]