[ CAS No. 10238-21-8 ] {[proInfo.proName]}

Name: 10238-21-8|5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide|98%
Brand: Ambeed
SKU: A212350
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Quality Control of [ 10238-21-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 10238-21-8 ]

SDS Specification

Alternatived Products of [ 10238-21-8 ]

Product Details of [ 10238-21-8 ]

CAS No. :	10238-21-8	MDL No. :	MFCD00056625
Formula :	C₂₃H₂₈ClN₃O₅S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZNNLBTZKUZBEKO-UHFFFAOYSA-N
M.W :	494.00	Pubchem ID :	3488
Synonyms :	Glyburide

Calculated chemistry of [ 10238-21-8 ]

Physicochemical Properties

Num. heavy atoms :	33
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.39
Num. rotatable bonds :	11
Num. H-bond acceptors :	5.0
Num. H-bond donors :	3.0
Molar Refractivity :	126.25
TPSA :	121.98 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.81
Log Po/w (XLOGP3) :	4.81
Log Po/w (WLOGP) :	4.72
Log Po/w (MLOGP) :	2.17
Log Po/w (SILICOS-IT) :	3.0
Consensus Log Po/w :	3.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.48
Solubility :	0.00165 mg/ml ; 0.00000334 mol/l
Class :	Moderately soluble
Log S (Ali) :	-7.1
Solubility :	0.0000389 mg/ml ; 0.0000000787 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-7.71
Solubility :	0.00000963 mg/ml ; 0.0000000195 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	3.34

Safety of [ 10238-21-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P273-P301+P312-P330	UN#:	N/A
Hazard Statements:	H302-H413	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 10238-21-8 ]

* 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 [ 10238-21-8 ]
Downstream synthetic route of [ 10238-21-8 ]

[ 10238-21-8 ] Synthesis Path-Upstream 1~11

1
[ 16673-34-0 ]
[ 3173-53-3 ]
[ 10238-21-8 ]

Yield	Reaction Conditions	Operation in experiment
4.49 g	With 18-crown-6 ether; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 0 - 5℃; for 6 h; Reflux	3.69 g (10 mmol) of Compound IV was dissolved in 50 mL of DMF.1.34 g (12 mmol) of potassium tert-butoxide and 0.8 g (3 mmol) of 18-crown-6 ether are added;Cyclohexyl isocyanate is dissolved in DMF,Formulated as a 1mol/L solution13 mL of this solution was added dropwise to the solution of compound IV at 0-5°C.After it is completely added,Warming to reflux reaction for 6h,Pour into 1N dilute hydrochloric acid at 0-5°C,Filtering,Vacuum drying4.49 g (9.1 mmol) of glyburide was obtained.

Reference： [1] Chemical Communications, 2014, vol. 50, # 40, p. 5248 - 5250
[2] Journal of Organic Chemistry, 2016, vol. 81, # 23, p. 11788 - 11801
[3] Patent: CN107879955, 2018, A, . Location in patent: Paragraph 0052

2
[ 201230-82-2 ]
[ 108-91-8 ]
[ 10238-21-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 18, p. 5545 - 5549[2] Angew. Chem., 2016, vol. 128, # 18, p. 5635 - 5639,5

3
[ 3438-16-2 ]
[ 10238-21-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 18, p. 5545 - 5549[2] Angew. Chem., 2016, vol. 128, # 18, p. 5635 - 5639,5
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 18, p. 5545 - 5549[4] Angew. Chem., 2016, vol. 128, # 18, p. 5635 - 5639,5
[5] Journal of Organic Chemistry, 2016, vol. 81, # 23, p. 11788 - 11801

4
[ 33924-49-1 ]
[ 10238-21-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 18, p. 5545 - 5549[2] Angew. Chem., 2016, vol. 128, # 18, p. 5635 - 5639,5
[3] Journal of Organic Chemistry, 2016, vol. 81, # 23, p. 11788 - 11801

5
[ 64-04-0 ]
[ 10238-21-8 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 23, p. 11788 - 11801
[2] Patent: CN107879955, 2018, A,

6
[ 29568-33-0 ]
[ 10238-21-8 ]

7
[ 33924-54-8 ]
[ 10238-21-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 18, p. 5545 - 5549[2] Angew. Chem., 2016, vol. 128, # 18, p. 5635 - 5639,5

8
[ 16673-34-0 ]
[ 10238-21-8 ]

Reference： [1] Patent: CN106278960, 2017, A,

9
[ 458-85-5 ]
[ 10238-21-8 ]

Reference： [1] Patent: CN107879955, 2018, A,

10
[ 223253-87-0 ]
[ 10238-21-8 ]

Reference： [1] Patent: CN107879955, 2018, A,

11
[ 155021-30-0 ]
[ 10238-21-8 ]
[ 7585-39-9 ]

Reference： [1] Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2010, vol. 68, # 3-4, p. 417 - 421

[ 10238-21-8 ] Synthesis Path-Downstream 1~70

1
[ 85-44-9 ]
[ 10238-21-8 ]
[ 2133-65-5 ]
[ 16673-34-0 ]

Reference： [1]Archiv der Pharmazie,1986,vol. 319,p. 682 - 690

2
[ 10238-21-8 ]
[ 2133-65-5 ]
[ 16673-34-0 ]

Reference： [1]Archiv der Pharmazie,1986,vol. 319,p. 682 - 690

3
[ 10238-21-8 ]
[ 108-24-7 ]
N-<4-<2-(5-Chlor-2-methoxybenzoylamino)ethyl>benzolsulfonyl>acetamid [ No CAS ]

Reference： [1]Archiv der Pharmazie,1986,vol. 319,p. 682 - 690

4
[ 10238-21-8 ]
C₂₃H₂₇⁽³⁾HClN₃O₅S [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 291 - 298

Yield	Reaction Conditions	Operation in experiment
94%	With palladium diacetate; In acetonitrile; at 20℃; under 20.0 Torr; for 12h;	General procedure: 25 ml two-port bottle adding Pd (OAc)2(1 mg, 0 . 004mmol), paratoluene sulfonyl azide (79 mg, 0 . 40mmol), morpholine (42 mg, 0 . 48mmol), acetonitrile 4 ml, the system vacuum to 20mmHg, then fill the CO gas to the atmospheric pressure, such repeated 3 times. The system is put in room temperature vigorously under stirring for 12 hours, the pressure of the solvent, the residue by column chromatography separation and purification (dichloromethane: methanol (volume ratio)=10:1), to obtain white solid product 111 mg, yield 93%.
		and the further antidiabetic compound is selected from the group consisting of ... rosiglitazone, pioglitazone, troglitazone, glisoxepid, glyburide, glibenclamide, acetohexamide, chloropropamide, ...
		EXAMPLE 4 A process similar to the process described in Example 2 yielded tablets containing 5.0 mg of glyburide.

		and the further antidiabetic compound is selected from the group consisting of ... pioglitazone, troglitazone, glisoxepid, glyburide, glibenclamide, acetohexamide, chloropropamide, glibornuride, ...
		Using this method the following compounds were prepared. ... 3. Chloroquine 4. Tamoxifen 5. Ibuprofen 6. Propranolol 7. Glyburide
		Preferred are pharmaceutical preparations containing at least one substituted 2-phenylbenzimidazole of formula IA or IA1 as well as an active substance selected from among: ... denileukin, etanercept, farglitazar, fidarestat, glibenclamide, glibornuride, gliclazide, glimepiride, ...

6
[ 10238-21-8 ]
[ 57334-90-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2003,vol. 46,p. S352 - S352

7
[ 10238-21-8 ]
[ 77-86-1 ]
[ 873552-77-3 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 5℃;	[00200] Glyburide (20.39 mg) and TRIS (tromethamine, 5 mg) were mixed in1 :1 mole ratio in 5 mL of methanol. The solution was kept overnight at 5 degrees C,decanted, and evaporated to dryness. DSC, TGA, and PXRD analyses were completedon the glyburide: TRIS co-crystal.[00201] DSC thermogram shows an endothermic transition at about 140 degreesC (Figure 1). TGA thermogram shows a weight loss of about 20 percent between about150 degress C and about 200 degrees C (Figure 2).[00202] The glyburide:TRIS co-crystal can be characterized by any one, anytwo, any three, any four, any five, or any six or more of the peaks in Figure 3 including,but not limited to, 5.29, 8.19, 12.23, 13.99, 15.43, 15.91, 17.31, 19.07, 22.01, 23.21,23.87, 25.61, and 26.41 degrees 2-theta (data as collected). Figure 3 shows the PXRDdiffractogram of the glyburide:TRIS co-crystal without background subtraction

Reference： [1]Patent: WO2006/7448,2006,A2 .Location in patent: Page/Page column 57

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 8 2,3,4,5,6-Pentafluoro-N-[2-(4-[[[(2,3,4-trifluorophenyl]carbonyl]amino]-sulfonyl)phenyl]ethyl]benzamide The methods outlined in Example 5, were used with 2,3,4-trifluorophenylisocyanate instead of cyclohexyl isocyanate to provide the desired glyburide analog. C22H13F8N3O4S Mol. Wt.: 567.05 Calcd. C, 46.57; H, 2.31; F, 26.79; N, 7.41; S, 5.65 Found C, 46.14; H, 2.05; F, 26.46; N, 7.14; S, 5.35

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 9 2,3,4,5,6-Pentafluoro-N-[2-(4-[[[(2,3,4,5,6-pentafluorophenyl]carbonyl]-amino]sulfonyl)phenyl]ethyl]benzamide The methods outlined in Example 8, were used with pentafluorophenyl isocyanate instead of 2,3,4-trifluorophenylisocyanate to provide the desired glyburide analog. C22H11F10N3O4S Mol. Wt.: 603.39 Calcd. C, 43.79; H, 1.84; F, 31.49; N, 6.96; S, 5.31 Found C, 43.43; H, 2.02; F, 31.33; N, 6.66; S, 5.36

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 7 3,5-Di(trifluoromethyl)phenyl-N-[2-(4-[[[(cyclohexylamino]carbonyl]amino]-sulfonyl)-phenyl]ethyl]benzamide The methods outlined in Example 5 were used with 3,5-di(trifluoromethyl)benzoic acid instead of 2,3,5,6-tetrafluoroterephthalic acid to provide the desired glyburide analog. C24H25F6N3O4S Mol. Wt.: 565.53 Calcd. C, 50.97; H, 4.46; F, 20.16; N, 7.43; S, 5.67 Found C, 50.68; H, 4.17; F, 20.00; N, 7.21; S, 5.27

Yield	Reaction Conditions	Operation in experiment
		A. A mixture of cyclohexylamine (2.98 g.) and ethylene carbonate (2.64 g.) was heated at 40-50 for 20 hours. p-(2-{5-chloro-2-methoxybenzamido}ethyl)-benzene sulfonamide (5.87 g. as sodium salt) and DMF (50 ml.) were added and the mixture heated at 110 for 3 hours. The solvent was evaporated in vacuo and the residue was treated with water (120 ml.). Unreacted sulfonamide (1.8 g.) thereby precipitated was filtered off. Crude 1-[p-(2-{5-chloro-2-methoxybenzamido}ethyl)-benzensulfonyl]-3-cyclohexyl urea was obtained from the acidified filtrate and crystallized twice from methanol to give the required sulfonylurea, m.p. 166-9 (i-r identical with authentic sample).

12
[ 23911-26-4 ]
[ 10238-21-8 ]
[ 848488-96-0 ]