[ CAS No. 2632-13-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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Quality Control of [ 2632-13-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2632-13-5 ]

SDS Specification

Alternatived Products of [ 2632-13-5 ]

Product Citations

Deciphering the Therapeutic Potential of Novel Pentyloxyamide-Based Class I, IIb HDAC Inhibitors against Therapy-Resistant Leukemia

Fabian Fischer ; Julian Schliehe-Diecks ; Jia-Wey Tu , et al. JMC,2024. DOI: 10.1021/acs.jmedchem.4c02024 PubMed ID: 39602240

Abstract: Histone deacetylase inhibitors (HDACi) are established anticancer drugs, especially in hematological cancers. This study aimed to design, synthesize, and evaluate a set of HDACi featuring a pentyloxyamide connecting unit linker region and substituted phenylthiazole cap groups. A structural optimization program yielded HDACi with nanomolar inhibitory activity against histone deacetylase class I/IIb enzymes. The novel inhibitors (4d and 4m) showed superior antileukemic activity compared to several approved HDACi. Furthermore, 4d and 4m displayed synergistic activity when combined with chemotherapeutics, decitabine, and clofarabine. In vitro pharmacokinetic studies showed the most promising profile for 4d with intermediate microsomal stability, excellent plasma stability, and concentration-independent plasma protein binding. Additionally, 4d demonstrated comparable in vivo pharmacokinetics to vorinostat. When administered in vivo, 4d effectively inhibited the proliferation of leukemia cells without causing toxicity. Furthermore, the binding modes of 4d and 4m to the catalytic domain 2 of HDAC6 from Danio rerio were determined by X-ray crystallography.

Purchased from AmBeed: 5000-65-7 ; 2632-13-5 ; 31949-21-0 ; 94790-37-1

Product Details of [ 2632-13-5 ]

CAS No. :	2632-13-5	MDL No. :	MFCD00000201
Formula :	C₉H₉BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XQJAHBHCLXUGEP-UHFFFAOYSA-N
M.W :	229.07	Pubchem ID :	4965
Synonyms :	NSC 1291; 4-(Bromoacetyl)anisole	Chemical Name :	2-Bromo-1-(4-methoxyphenyl)ethanone

Calculated chemistry of [ 2632-13-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.0
TPSA :	26.3 ?2

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) :	-5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	2.53
Log Po/w (WLOGP) :	2.27
Log Po/w (MLOGP) :	1.89
Log Po/w (SILICOS-IT) :	2.71
Consensus Log Po/w :	2.3

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.03
Solubility :	0.216 mg/ml ; 0.000942 mol/l
Class :	Soluble
Log S (Ali) :	-2.73
Solubility :	0.428 mg/ml ; 0.00187 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.74
Solubility :	0.0419 mg/ml ; 0.000183 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.49

Safety of [ 2632-13-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310	UN#:	3261
Hazard Statements:	H302+H312+H332-H314-H290	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 2632-13-5 ]

* 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 [ 2632-13-5 ]
Downstream synthetic route of [ 2632-13-5 ]

[ 2632-13-5 ] Synthesis Path-Upstream 1~1

1
[ 2632-13-5 ]
[ 92409-15-9 ]

Reference： [1] Green Chemistry, 2016, vol. 18, # 24, p. 6545 - 6555

[ 2632-13-5 ] Synthesis Path-Downstream 1~10

1
[ 13623-11-5 ]
[ 2632-13-5 ]
[ 958-64-5 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1964,vol. 679,p. 139 - 144

2
[ 5319-77-7 ]
[ 2632-13-5 ]
2-(2-imino-5-methylsulfanyl-[1,3,4]thiadiazol-3-yl)-1-(4-methoxy-phenyl)-ethanone [ No CAS ]

Reference： [1]Pharmazie,1979,vol. 34,p. 144 - 147

3
[ 57508-48-2 ]
[ 2632-13-5 ]
[ 173458-92-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium ethanolate; In ethanol; at 0 - 20℃;	To the solution of EtONa (4.08 g, 60 mmol) in EtOH (60 mL) was added compound 104 (10 g, 60 mmol) at 0 0C under nitrogen. The mixture was stirred for 20 minutes and 2-bromo-4'-methyloxy-acetophenone was added. After stirring at room temperature overnight, the mixture was concentrated and the residue was taken up in ethyl acetate, washed with water, brine, dried and concentrated to give a residue which was purified by column chromatography to afford the product 402 as a solid (5.2 g, 67 %yield). 1H NMR (DMSOd6) delta 10.62 (s, IH), 7.41 (d, J = 6.6 Hz, 2H), 6.88 (d, J = 6.6 Hz, 2H), 6.30 (d, J = 3.0 Hz, IH), 5.59 (s, 2H), 4.13 (q, J = 6.9 Hz, 2H), 3.74 (s, 3H), 1.24 (t, J = 7.2 Hz, 3 H). LC-MS: 260 (M+l).
67%		To the solution of EtONa (4.08 g, 60 mmol) in EtOH (60 mL) was added compound 104 (10 g, 60 mmol) at 0 0C under nitrogen. The mixture was stirred for20 minutes and 2-bromo-4'-methyloxy-acetophenone was added. After stirring at room temperature overnight, the mixture was concentrated and the residue was taken up in ethyl acetate, washed with water, brine, dried and concentrated to give a residue which was purified by column chromatography to afford the product 402 as a solid (5.2 g, 67 %yield). 1H NMR (DMSO-d6) delta 10.62 (s, 1eta), 7.41 (d, J = 6.6 Hz,2H), 6.88 (d, J = 6.6 Hz, 2H), 6.30 (d, J = 3.0 Hz, IH), 5.59 (s, 2H), 4.13 (q, J = 6.9 Hz, 2H), 3.74 (s, 3H), 1.24 (t, J = 7.2 Hz, 3 H). LC-MS: 260 (M+l).
		General procedure: The following is representative: <strong>[57508-48-2]ethyl 3-amino-3-iminopropanoate hydrochloride</strong> (3) (8.3 g, 50.0 mmol) and NaOEt (5.1 g, 75.0 mmol) were dissolved in abs. EtOH at 0 C and stirred for 20 min under argon. The mixture was heated to 60 C, and 2-bromo-1-phenylethanone (4b) (5.0 g, 25.0 mmol) was added portion wise over 5 min. After 1.5 h the mixture was cooled to 20 C and the solvent was evaporated under reduced pressure. The residue was diluted with distilled water (20 mL) and extracted with EtOAc (3 × 80 mL). The organic layer was washed with water (3 × 20 mL) and brine (3 × 20 mL). The combined water fractions were back extracted with EtOAc (2 × 20 mL). The organic phases were dried over MgSO4, and the solvent was evaporated under reduced pressure. Purification was by silica-gel column chromatography (EtOAc/n-pentane, 7/3).

Reference： [1]Magnetic Resonance in Chemistry,2010,vol. 48,p. 244 - 248
[2]Patent: WO2008/33745,2008,A2 .Location in patent: Page/Page column 65
[3]Patent: WO2008/33747,2008,A2 .Location in patent: Page/Page column 250
[4]European Journal of Medicinal Chemistry,2011,vol. 46,p. 6002 - 6014

4
[ 141-52-6 ]
[ 57508-48-2 ]
[ 2632-13-5 ]
[ 173458-92-9 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	Step 12.1: 2-Amino-3-ethoxycarbonyl-5-(4-methoxy-phenyl)-1H-pyrrole Analogously to Step 8.1, 1.67 g (10 mmol) of 2-amidino-acetic acid ethyl ester hydro-chloride in 20 ml of abs. ethanol are reacted with 716 mg (10 mmol) of sodium ethanolate and 1.145 g (5.0 mmol) of 4-methoxy-phenacyl bromide (Fluka; Buchs/Switzerland) to form the title compound; m.p. 141-142 C.; TLC-Rf =0.4 (hexane/ethyl acetate [1:1]); FAB-MS: (M+H)+ =261.

Reference： [1]Patent: US6140332,2000,A

5
[ 36193-65-4 ]
[ 2632-13-5 ]
[ 1178571-98-6 ]

Reference： [1]Synlett,2009,p. 1463 - 1465

6
[ 2632-13-5 ]
[ 374750-30-8 ]
[ 1188418-36-1 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 3845 - 3851

7
[ 13599-12-7 ]
[ 2632-13-5 ]
[ 1245459-03-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4766 - 4770
[2]European Journal of Medicinal Chemistry,2010,vol. 45,p. 5792 - 5799
[3]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2011,vol. 81,p. 372 - 379

8
[ 13599-12-7 ]
[ 2632-13-5 ]
[ 1338328-32-7 ]

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2011,vol. 81,p. 372 - 379

9
[ 57508-48-2 ]
[ 2632-13-5 ]
[ 173458-92-9 ]
[ 4136-21-4 ]
[ 58518-78-8 ]
[ 171119-05-4 ]

Reference： [1]Bioorganic Chemistry,2012,vol. 44,p. 35 - 41,7

10
[ 2632-13-5 ]
[ 17583-10-7 ]
2-(4-methoxyphenyl)-6,7-dihydrobenzo[d]imidazo[2,1-b]-thiazol-8(5H)-one [ No CAS ]

Reference： [1]Archiv der Pharmazie,2019,vol. 352

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Isomers

Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Halogenation of Phenols ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Related Functional Groups of
[ 2632-13-5 ]

Aryls

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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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[ CAS No. 2632-13-5 ] {[proInfo.proName]}

Quality Control of [ 2632-13-5 ]

Related Doc. of [ 2632-13-5 ]

Product Citations

Product Details of [ 2632-13-5 ]

Calculated chemistry of [ 2632-13-5 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2632-13-5 ]

Application In Synthesis of [ 2632-13-5 ]

[ 2632-13-5 ] Synthesis Path-Upstream 1~1

[ 2632-13-5 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 2632-13-5 ]

Aryls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2632-13-5 ]