[ CAS No. 348-40-3 ] {[proInfo.proName]}

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Quality Control of [ 348-40-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 348-40-3 ]

SDS Specification

Alternatived Products of [ 348-40-3 ]

Product Citations

Novel amides of mycophenolic acid and some heterocyclic derivatives as immunosuppressive agents

Walczak, Juliusz Maksymilian ; Iwaszkiewicz-Grzes, Dorota ; Ziomkowska, Michalina , et al. J. Enzym. Inhib. Med. Ch.,2022,37(1):2725-2741. DOI: 10.1080/14756366.2022.2127701 PubMed ID: 36189734

Abstract: The group of 18 new amide derivatives of mycophenolic acid (MPA) and selected heterocyclic amines was synthesised as potential immunosuppressive agents functioning as inosine-5′-monophosphate dehydrogenase (IMPDH) uncompetitive inhibitors. The synthesis of 14 of them employed uronium-type activating system (TBTU/HOBt/DIPEA) while 4 of them concerned phosphonic acid anhydride method (T3P/Py) facilitating amides to be obtained in moderate to excellent yields without the need of phenolic group protection. Most of optimised protocols did not require complicated reaction work-ups, including chromatographic, solvent-consuming methods. The biological activity assay was performed on the T-Jurkat cell line and peripheral mononuclear blood cells (PBMCs) which are both dedicated for antiproliferative activity determination. Each of designed derivatives was characterised by reduced cytotoxicity and benzoxazole analogue (A2) revealed the most promising activity. Subsequently, an observed structure-activity relationship was discussed.

Keywords: Mycophenolic acid ; amide derivatives ; heterocycles ; benzoxazole ; IMPDH inhibition

Purchased from AmBeed: 934-32-7 ; 1477-42-5 ; 5464-79-9 ; 5464-79-9 ; 136-95-8 ; 95-24-9 ; 533-30-2 ; 1123-93-9 ; 6285-57-0 ; 15864-32-1 ; 29927-08-0 ; 348-40-3 ; 58-63-9 ; 4570-41-6 ; 75985-45-4 ; 24280-93-1 ; 2536-91-6 ; 19952-47-7 ; 1747-60-0 ; 777-12-8 ; 58-63-9 ; 63837-12-7 ...More

Product Details of [ 348-40-3 ]

CAS No. :	348-40-3	MDL No. :	MFCD00013336
Formula :	C₇H₅FN₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CJLUXPZQUXVJNF-UHFFFAOYSA-N
M.W :	168.19	Pubchem ID :	319954
Synonyms :

Calculated chemistry of [ 348-40-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.98
TPSA :	67.15 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.67
Log Po/w (XLOGP3) :	2.06
Log Po/w (WLOGP) :	2.45
Log Po/w (MLOGP) :	1.69
Log Po/w (SILICOS-IT) :	2.85
Consensus Log Po/w :	2.14

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.79
Solubility :	0.275 mg/ml ; 0.00164 mol/l
Class :	Soluble
Log S (Ali) :	-3.1
Solubility :	0.134 mg/ml ; 0.000796 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.88
Solubility :	0.22 mg/ml ; 0.00131 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.15

Safety of [ 348-40-3 ]

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 [ 348-40-3 ]

* 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 [ 348-40-3 ]

[ 348-40-3 ] Synthesis Path-Downstream 1~5

1
[ 348-40-3 ]
[ 78364-55-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogenchloride; hydrazine hydrate; In water; at 5℃; for 5h;Reflux;	6-Fluoro-2-hydrazinobenzothiazole (2). Hydrochloric acid (10 mL) was added dropwise to hydrazine hydrate 99% (10 g, 0.2 mol) at 5-10 C, followed by addition of a solution of 2-amino-6-fluorobenzothiazole (1) (3.364 g, 0.02 mol) in ethylene glycol (40 mL). The mixture was heated at reflux temperature for 5 h. On cooling, the precipitated solid was collected by filtration, washed with water, dried and crystallized from ethanol. Yield 89%, m.p. 194-196 C [1].
	With hydrazine hydrochloride; hydrazine hydrate; In ethylene glycol; at 140℃; for 2h;	General procedure: The substituted aniline (1eq.) and ammonium thiocyanate (2eq.) in 150mL glacial acetic acid were cooled in an ice bath and stirred mechanically. To the sulution, bromine (2eq.) in 25ml glacial acetic acid was added dropwise at such arate to keep the temperature below 10oC throughout the addition. Stirring was continued for additional 30 min after the bromine addition. The precipitate was collected and recrystallization from ethanol to give 2-aminobenzthiazoles. Then, the substituted 2-aminobenzthiazoles (1eq) in ethylene glycol were added hydrazine hydrate (2eq.) and hydrazine dihydrochloride (2eq). The mixture was heated at 140 oC for 2h. After cooling, the precipitate was filtered to give used directly for next step without further purification. Then, the hydrazino compound was added to thionyl chloride (1eq.) for 2h at 50 oC. After evaporated under reduced pressure, the residue was taken up in ethyl acetate and washed with 1 M NaHCO3 and brine each for twice. The organic layer was dried and evaporated to give the crude final product. The crude product was purified by silica gel column chromatography using PE-EA as an eluent.
	With hydrogenchloride; hydrazine hydrate; In water; ethylene glycol; at 5℃; for 5h;Reflux;	Hydrochloric acid (10 mL) was added dropwise to hydrazine hydrate 99% (10 g, 0.2 mol) at 5-10 C, followed by addition of a solution of 2-amino-6-fluorobenzothiazole (1) (3.364 g, 0.02 mol) in ethylene glycol (40 mL). The mixture was heated at reflux temperature for 5 h. On cooling, the precipitated solid was collected by filtration, washed with water, dried and crystallized from ethanol. Yield 89%, m.p. 194-196 C [1].

With hydrogenchloride; hydrazine hydrate; In water; ethylene glycol; at 5℃;Reflux;

Concentrated hydrochloric acid (0.067 mol) was added dropwise with stirring tohydrazine hydrate (0.12 mol) at 5-6 C followed by ethylene glycol (30 mL);thereafter, 6-uorobenzo[d]thiazol-2-amine (1) (20 mmol) was added in portionsand the resultant mixture was reuxed for 2-3 h and cooled at room temperature.The reaction progress was monitored by TLC using toluene:ethylacetate (75:25) asmobile phase. The reaction mixture was ltered and the resulting precipitates werewashed with distilled water. The resulting crude was recrystallized from ethanol. IR(KBr) mmax: 3010 (=C-H str), 1645 (C=C str), 1398 (C=N str). The 1HNMR(DMSO-d6) spectrum of this product showed signals: d 7.2-7.4 (3H, m, Ar C-H), at4.0 (1H, br, NH) and 4.75 (2H, br, NH2) ppm. The peaks in its 13CNMR (DMSO-d6)d: 106.1, 112.4, 115.5, 129.7, 145.5, 157.5, 171.2 ppm.

Reference： [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. 459 - 465
[2]Chinese Chemical Letters,2015,vol. 26,p. 1522 - 1528
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4022 - 4025
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. <B> 20,p. 314 - 316
[5]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4293 - 4299
[6]Archiv der Pharmazie,2010,vol. 343,p. 692 - 699
[7]Journal of Enzyme Inhibition and Medicinal Chemistry,2011,vol. 26,p. 527 - 534
[8]Journal of the Indian Chemical Society,2008,vol. 85,p. 333 - 335
[9]Chemistry and biodiversity,2011,vol. 8,p. 253 - 265
[10]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3044 - 3049
[11]Journal of Medicinal Chemistry,2013,vol. 56,p. 5514 - 5540
[12]Chinese Chemical Letters,2016,vol. 27,p. 380 - 386
[13]Chemical Biology and Drug Design,2016,p. 354 - 362
[14]Research on Chemical Intermediates,2016,vol. 42,p. 8329 - 8344
[15]Journal of Medicinal Chemistry,2019
[16]New Journal of Chemistry,2019,vol. 43,p. 7150 - 7161

2
[ 348-40-3 ]
[ 7787-70-4 ]
[ 152937-04-7 ]

Yield	Reaction Conditions	Operation in experiment
40%	With tert.-butylnitrite; In hexane; ethyl acetate; acetonitrile;	(Step 1) Synthesis of 2-bromo-6-fluorobenzothiazole Copper (I) bromide (619 mg, 4.32 mmol) was suspended in acetonitrile (10 ml). To the resulting suspension was added tert-butyl nitrite (640 ael, 5.38 mmol), followed by stirring at 60ØC for 5 minutes. To the reaction mixture was added 2-amino-6-fluorobenzothiazole (605 mg, 3.60 mmol). The resulting mixture was stirred at 60ØC for 10 minutes. After cooling to the room temperature, the reaction mixture was diluted with ethyl acetate. The ethyl acetate solution was washed with 1N HCl, saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ ethyl acetate (5:1, v/v) eluate fractions, 2-bromo-6-fluorobenzothiazole (330 mg, 40%) was obtained as a brown solid. 1H-NMR (CDCl3) delta: 7.19-7.24 (m, 1H), 7.49-7.52 (m, 1H), 7.92-7.96 (m, 1H). MS (ESI) m/z 273.8 (M++1+MeCN).
	With sodium nitrite; In water; hydrogen bromide;	EXAMPLE 28 [(2-(6-Fluorobenzothiazolyl))carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester STR36 Slurry 2-amino-6-fluorobenzothiazole (0.255 mol) in water (325 mL), heat to reflux and add 48% hydrobromic acid (130 mL). Maintain at reflux for 20 minutes, cool to 0 C. and add a solution of sodium nitrite (17.56 g, 0.255 mol) water (90 mL), maintaining a temperature of 0 C. Stir at 0 C. for 15 minutes and add by dropwise addition (while keeping cold) to a rapidly stirring mixture of copper (I) bromide (42.03 g, 0.293 mol) in 48% hydrobromic acid (86 mL) and water (225 mL). Stir at room temperature for 20 minutes. Allow to stand overnight, extract into methylene chloride and dry (MgSO4). Evaporate the solvent in vacuo and purify by chromatography to give 2-bromo-6-fluorobenzothiazole.

Reference： [1]Patent: EP1346982,2003,A1
[2]Patent: US5371093,1994,A

3
[ 348-40-3 ]
[ 152937-04-7 ]

Yield	Reaction Conditions	Operation in experiment
40%	With tert.-butylnitrite; copper(I) bromide; In acetonitrile; at 60.0℃; for 1.0h;	General procedure: To a stirred suspension of CuBr (1.57 g, 10.9 mmol) in MeCN (25 ml) was added tBuONO (1.63 ml, 13.7 mmol) and the mixture was stirred at 60 C for 10 min. Then 2-amino-6-methylbenzothiazole (14b) (1.50 g, 9.13 mmol) was added to the mixture, and the reaction mixture was stirred at 60 C for 1 h. After cooled to room temperature, the mixture was poured into 1 N HCl. The resulting precipitate was dissolved into EtOAc, washed with 1 N HCl, brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica gel with n-hexane-EtOAc (7:1, v/v) as eluent to give the title compound (703 mg, 34%) as a brown oil.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 1201 - 1212
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5919 - 5923

4
[ 348-40-3 ]
[ 41360-32-1 ]
C₁₅H₁₁FN₂O₄S₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9094 - 9106

5
[ 348-40-3 ]
[ 70395-35-6 ]
2-chloro-2-fluoro-N-(6-fluorobenzo[d]thiazol-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 3.0h;	General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.

Reference： [1]Chemical and Pharmaceutical Bulletin,2020,vol. 68,p. 1074 - 1081

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Technical Information

• Alkyl Halide Occurrence • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

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H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 348-40-3 ] {[proInfo.proName]}

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[ 348-40-3 ] Synthesis Path-Downstream 1~5

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