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2725-53-3 Usage

Uses

5-tert-Butyl-2-hydroxybenzaldehyde is a general chemical reactant/reagent used in the synthesis of Vanadium (V) amino phenolato antitumor agents. As well, its used in the synthesis of dibutyltin complexes for their cytotoxic activity.

Check Digit Verification of cas no

The CAS Registry Mumber 2725-53-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,7,2 and 5 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2725-53:
(6*2)+(5*7)+(4*2)+(3*5)+(2*5)+(1*3)=83
83 % 10 = 3
So 2725-53-3 is a valid CAS Registry Number.
InChI:InChI=1/C11H14O2/c1-11(2,3)9-4-5-10(13)8(6-9)7-12/h4-7,13H,1-3H3

2725-53-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-tert-butyl-2-hydroxybenzaldehyde

1.2 Other means of identification

Product number -
Other names Benzaldehyde, 5-(1,1-dimethylethyl)-2-hydroxy-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2725-53-3 SDS

2725-53-3Synthetic route

formaldehyd
50-00-0

formaldehyd

para-tert-butylphenol
98-54-4

para-tert-butylphenol

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With triethylamine; magnesium chloride In acetonitrile for 3h; Heating;98%
With triethylamine; magnesium chloride In acetonitrile for 3h; Reflux;98%
With triethylamine; magnesium chloride In acetonitrile for 8h; Reflux;96%
para-tert-butylphenol
98-54-4

para-tert-butylphenol

hexamethylenetetramine
100-97-0

hexamethylenetetramine

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid at 80℃; for 24h; Inert atmosphere;61.06%
Stage #1: para-tert-butylphenol; hexamethylenetetramine With trifluoroacetic acid at 120℃; for 0.5h; Microwave irradiation;
Stage #2: With water; potassium carbonate
46%
With trifluoroacetic acid for 1.5h; Heating;29%
With acetic acid
With boric acid; glycerol
chloroform
67-66-3

chloroform

para-tert-butylphenol
98-54-4

para-tert-butylphenol

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With sodium hydroxide In water for 8h; Inert atmosphere; Reflux;42.5%
With sodium hydroxide In methanol; water at 65℃; for 2h;27.3%
With sodium hydroxide In methanol; water at 65 - 70℃; for 3h;25%
2-aminomethyl-4-tert-butyl-phenol
81441-06-7

2-aminomethyl-4-tert-butyl-phenol

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With hexamethylenetetramine In acetic acid for 4h; Heating;17%
para-tert-butylphenol
98-54-4

para-tert-butylphenol

(CH2O)x

(CH2O)x

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
Stage #1: para-tert-butylphenol With magnesium methanolate In methanol; toluene for 1h; Heating;
Stage #2: (CH2O)x In toluene at 110℃; for 3h;
Stage #3: With sulfuric acid In toluene at 60℃; for 1.5h;
para-tert-butylphenol
98-54-4

para-tert-butylphenol

CH3MgO

CH3MgO

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
In methanol; toluene for 3h; Heating;
phenol
108-95-2

phenol

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: zinc chloride / 180 °C
2: NaOH; water
View Scheme
ethanol
64-17-5

ethanol

para-tert-butylphenol
98-54-4

para-tert-butylphenol

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With chloroform; potassium hydroxide In water at 60℃; for 15h; Reimer-Tiemann Phenol Formylation;
formaldehyd
50-00-0

formaldehyd

2-tert-Butylphenol
88-18-6

2-tert-Butylphenol

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With triethylamine; magnesium chloride In tetrahydrofuran for 5h; Inert atmosphere; Reflux;
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

5-(tert-butyl)-2-((tert-butyldimethylsilyl)oxy)benzaldehyde
1108723-71-2

5-(tert-butyl)-2-((tert-butyldimethylsilyl)oxy)benzaldehyde

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 15h;100%
With 1H-imidazole In dichloromethane at 0℃; Sealed tube;
With 1H-imidazole In dichloromethane at 0℃; Sealed tube;
With dmap; triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;
With 1H-imidazole In N,N-dimethyl-formamide
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

5-(tert-butyl)-2-hydroxybenzaldehyde oxime
50849-50-8

5-(tert-butyl)-2-hydroxybenzaldehyde oxime

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol at 60℃; for 3h;100%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 3h; Reflux;37%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol; water for 4h; Reflux;
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

N-(ethoxymethyl)-N-hexylhexan-1-amine

N-(ethoxymethyl)-N-hexylhexan-1-amine

5-tert-butyl-3-[(dihexylamino)methyl]-2-hydroxybenzaldehyde
494769-72-1

5-tert-butyl-3-[(dihexylamino)methyl]-2-hydroxybenzaldehyde

Conditions
ConditionsYield
In acetonitrile for 90h; Reflux; Inert atmosphere;99.1%
In acetonitrile for 72h; Heating;
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

3-nitro-5-tert-butyl-2-hydroxybenzaldehyde
85943-75-5

3-nitro-5-tert-butyl-2-hydroxybenzaldehyde

Conditions
ConditionsYield
With (NO)+18-crown-6-H(NO3)2 In ethyl acetate at 20℃; for 5h;99%
Stage #1: 2-hydroxy-5-t-butylbenzaldehyde With nitronium tetrafluoborate In acetonitrile at -30 - -15℃; for 1h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
94%
With nitric acid In acetic acid at 20℃; for 2h;61%
formaldehyd
50-00-0

formaldehyd

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

3-(bromomethyl)-5-(tert-butyl)-2-hydroxybenzaldehyde
367965-70-6

3-(bromomethyl)-5-(tert-butyl)-2-hydroxybenzaldehyde

Conditions
ConditionsYield
With sulfuric acid; hydrogen bromide at 70℃; for 96h;99%
With sulfuric acid; water; hydrogen bromide at 70℃; for 20h;98%
With sulfuric acid; hydrogen bromide In water at 70℃; for 24h;98%
formaldehyd
50-00-0

formaldehyd

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

3-(chloromethyl)-5-(tert-butyl)-2-hydroxybenzaldehyde

3-(chloromethyl)-5-(tert-butyl)-2-hydroxybenzaldehyde

Conditions
ConditionsYield
With hydrogenchloride; sulfuric acid at 70℃; for 20h; Inert atmosphere;99%
With hydrogenchloride; sulfuric acid In water at 70℃; for 120h; Inert atmosphere;96%
With hydrogenchloride; sulfuric acid; water at 70℃; for 45h;93%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

dimethylcarbamic acid 2-formyl-4-tert-butylphenyl ester
1581705-40-9

dimethylcarbamic acid 2-formyl-4-tert-butylphenyl ester

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper(l) chloride at 80℃; for 0.25h;99%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

vinylmagnesium chloride
3536-96-7

vinylmagnesium chloride

4-(tert-butyl)-2-(1-hydroxyallyl)phenol

4-(tert-butyl)-2-(1-hydroxyallyl)phenol

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere;99%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

1,4-bis(bromomethyl)-2,3,5,6-tetramethylbenzene
35168-64-0

1,4-bis(bromomethyl)-2,3,5,6-tetramethylbenzene

6,6'-((2,3,5,6-tetramethyl-1,4-phenylene)dimethylenedioxy)bis(3-(tert-butyl)dibenzaldehyde)

6,6'-((2,3,5,6-tetramethyl-1,4-phenylene)dimethylenedioxy)bis(3-(tert-butyl)dibenzaldehyde)

Conditions
ConditionsYield
With potassium carbonate In acetone for 10h; Reflux;99%
With potassium carbonate In acetone Inert atmosphere;99%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

C28H24N2S

C28H24N2S

C39H36N2OS

C39H36N2OS

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 24h; Reflux;98.6%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

5-tert-butyl-2-(methoxymethoxy)benzaldehyde
611227-43-1

5-tert-butyl-2-(methoxymethoxy)benzaldehyde

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;98%
With sodium hydroxide; Aliquat 336 In dichloromethane; water at -10℃; for 0.5h;88%
Stage #1: 2-hydroxy-5-t-butylbenzaldehyde With sodium hydride In tetrahydrofuran; mineral oil for 0.166667h;
Stage #2: chloromethyl methyl ether In tetrahydrofuran; toluene; mineral oil at 0 - 20℃; for 6h;
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

4-(tert-butyl)-2-(hydroxymethyl)phenol
6638-87-5

4-(tert-butyl)-2-(hydroxymethyl)phenol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; Inert atmosphere;98%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Schlenk technique; Reflux;95%
Stage #1: 2-hydroxy-5-t-butylbenzaldehyde With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; C6H13ClO2Si; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane Inert atmosphere;
77%
With sodium tetrahydroborate In methanol at 0 - 20℃; for 16h;67.6%
With methanol; sodium tetrahydroborate at 20℃; for 1h; Inert atmosphere;
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine

C17H19NO2

C17H19NO2

Conditions
ConditionsYield
for 0.1h; microwave irradiation;98%
(2-aminomethylpyridine)
3731-51-9

(2-aminomethylpyridine)

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

4-tert-butyl-2-{[(pyridin-2-ylmethyl)amino]methyl}phenol
790224-67-8

4-tert-butyl-2-{[(pyridin-2-ylmethyl)amino]methyl}phenol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol Inert atmosphere;98%
Stage #1: 2-(Aminomethyl)pyridine; 2-hydroxy-5-t-butylbenzaldehyde In ethanol at 60℃; for 10h;
Stage #2: With sodium tetrahydroborate In methanol; ethanol for 3h;
64%
tetrahydrofuran
109-99-9

tetrahydrofuran

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

5-tert-butyl-2-(tetrahydrofuran-2-yloxy)benzaldehyde
1581231-20-0

5-tert-butyl-2-(tetrahydrofuran-2-yloxy)benzaldehyde

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper(l) chloride In water at 100℃;98%
With tert.-butylhydroperoxide; diiron nonacarbonyl In decane at 110℃; chemoselective reaction;72%
N-(3-methylphenyl)hydroxylamine
620-25-7

N-(3-methylphenyl)hydroxylamine

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

C18H21NO2

C18H21NO2

Conditions
ConditionsYield
for 0.116667h; microwave irradiation;97%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

2,5-dibromomethyl-p-xylene
35168-62-8

2,5-dibromomethyl-p-xylene

C32H38O4

C32H38O4

Conditions
ConditionsYield
With potassium carbonate In acetone for 10h; Reflux; Inert atmosphere;97%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

dimethyl 2,2’-diamino-[1,1’-biphenyl]-4,4’-dicarboxylate
23933-57-5

dimethyl 2,2’-diamino-[1,1’-biphenyl]-4,4’-dicarboxylate

C38H40N2O6

C38H40N2O6

Conditions
ConditionsYield
With formic acid In ethanol at 20℃; for 48h;97%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Trimethylenediamine
109-76-2

Trimethylenediamine

2-((E)-(3-((E)-5-tert-butyl-2-hydroxybenzylideneamino)propylimino)methyl)-4-tert-butylphenol

2-((E)-(3-((E)-5-tert-butyl-2-hydroxybenzylideneamino)propylimino)methyl)-4-tert-butylphenol

Conditions
ConditionsYield
In ethanol for 1.5h; Reflux;96.1%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

C18H21NO2

C18H21NO2

Conditions
ConditionsYield
for 0.116667h; microwave irradiation;96%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

N-(4-chlorophenyl)hydroxylamine
823-86-9

N-(4-chlorophenyl)hydroxylamine

C17H18ClNO2

C17H18ClNO2

Conditions
ConditionsYield
for 0.1h; microwave irradiation;96%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

benzyl bromide
100-39-0

benzyl bromide

2-(benzyloxy)-5-tert-butylbenzaldehyde
796047-09-1

2-(benzyloxy)-5-tert-butylbenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 5h;96%
With potassium carbonate In N,N-dimethyl-formamide
With potassium carbonate In acetone at 20℃; for 8h; Schlenk technique; Glovebox;
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

methyl iodide
74-88-4

methyl iodide

5-tert-butyl-2-methoxybenzaldehyde
85943-26-6

5-tert-butyl-2-methoxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h;96%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere;94%
In acetonitrile at 20℃;94%
With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 13h; Inert atmosphere;
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

(2S)-3-exo-aminoisoborneol
41719-73-7

(2S)-3-exo-aminoisoborneol

(1R,2S,3R,4S)-(+)-3-[(2-hydroxy-5-tert-butyllbenzylidene)amino]isoborneol

(1R,2S,3R,4S)-(+)-3-[(2-hydroxy-5-tert-butyllbenzylidene)amino]isoborneol

Conditions
ConditionsYield
With sodium sulfate In methanol; dichloromethane for 12h; Inert atmosphere; Reflux;96%
(1S,2R)-2-Amino-1,2-diphenylethanol
23364-44-5

(1S,2R)-2-Amino-1,2-diphenylethanol

2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

(1S,2R)-tBu(OH)(C6H3)CHN(CHPh)2OH
1383616-98-5

(1S,2R)-tBu(OH)(C6H3)CHN(CHPh)2OH

Conditions
ConditionsYield
With sodium sulfate In methanol at 20℃; for 15h;96%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

C12H16N2
857776-15-9

C12H16N2

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

C25H27F3N2O2

C25H27F3N2O2

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-t-butylbenzaldehyde; C12H16N2 In chloroform at -40℃; for 8h; Molecular sieve;
Stage #2: trifluoroacetic anhydride In chloroform at -40℃; Molecular sieve;
96%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

1,5,9-triamino-2,3,6,7,10,11-hexabutoxybenzophenanthrene

1,5,9-triamino-2,3,6,7,10,11-hexabutoxybenzophenanthrene

C63H63N3O6

C63H63N3O6

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-t-butylbenzaldehyde; 1,5,9-triamino-2,3,6,7,10,11-hexabutoxybenzophenanthrene With 1-methyl-pyrrolidin-2-one; trifluorormethanesulfonic acid at 120℃; for 12h; Pictet-Spengler Synthesis;
Stage #2: With potassium carbonate at 120℃; for 12h;
96%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

3-bromo-5-tert-butyl-2-hydroxy-benzaldehyde
119646-68-3

3-bromo-5-tert-butyl-2-hydroxy-benzaldehyde

Conditions
ConditionsYield
With bromine; sodium acetate; acetic acid at 50℃; for 12h;95%
With bromine; sodium acetate In acetic acid at 50℃; for 12h;95%
With bromine; acetic acid at 50℃; for 18h;93%
2-hydroxy-5-t-butylbenzaldehyde
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

i-C3H7-Mg-X

i-C3H7-Mg-X

4-tert-Butyl-2-(1-hydroxy-2-methyl-propyl)-phenol
96126-92-0

4-tert-Butyl-2-(1-hydroxy-2-methyl-propyl)-phenol

Conditions
ConditionsYield
In diethyl ether for 2h; Ambient temperature;95%

2725-53-3Relevant articles and documents

A novel axially palladium(II)-Schiff base complex substituted silicon(IV) phthalocyanine: Synthesis, characterization, photophysicochemical properties and photodynamic antimicrobial chemotherapy activity against Staphylococcus aureus

Sen, Pinar,Nyokong, Tebello

, (2019)

In this study, a novel silicon(IV) phthalocyanine is reported for the first time as a phthalocyanine derivative bearing axially a palladium(II)-Schiff base complex. The photophysical and photochemical properties of the new Si(IV)Pc, such as absorption, fluorescence, singlet oxygen quantum yields, triplet state quantum yields and exited state lifetimes were measured in DMSO. The new silicon phthalocyanine displayed very low fluorescence, showing efficient intersystem crossing resulting in high triplet and high singlet oxygen quantum yields in DMSO. When compared with the unsubstituted SiPcCl2, the singlet oxygen quantum yield value (ΦΔ = 0.47) in relation to the triplet quantum yield (ΦT = 0.82), which is an important determinant for PDT applications, increased. The photodynamic antimicrobial chemotherapy activity (PACT) of new Si(IV)Pc towards Staphylococcus aureus was determined in comparison to the unsubstituted SiPcCl2. The results of the photodynamic antimicrobial effect study demonstrated that the Pd(II) complex substituted SiPc (5) possesses excellent photodynamic activity with a reduction percentage value of 99.94% and a log red value of 3.26.

Zwitterionic macrocyclic metal sulfate extractants containing 3-dialkylaminomethylsalicylaldimine units

Plieger, Paul G.,Tasker, Peter A.,Galbraith, Stuart G.

, p. 313 - 318 (2004)

10,25-Di-tert-alkyl-14,21-dimethyl-3,6,14,21-tetraazatricyclo[21.3.1.18, 12]octacosa-1(27),2,6,8,10,12(28),23,25-octaene-27,28-diol macrocycles form Ni(II) and Cu(II) complexes in which the metal cation and the sulfate anion are bound in separated sites in a zwitterionic form of the ligand. The nonyl-substituted macrocycle shows a higher affinity for SO42- and a lower binding strength for Cu2+ than open chain analogues, the pH-dependences for which fall in ranges which allow loading of CuSO4 at pH ≈4 and easy stripping to recycle the ligand. X-Ray structure determinations of the Cu(II) and Ni(II) sulfate complexes of the tert-butyl substituted ligand suggest that the de-tuning of M2+-binding results from a distortion from planarity of the "salen" N2O22- donor set imposed by the incorporation of the hexamethylene strap in the ligand and reveal that the sulfate is bound as a hydrate in a 2:2:2:2, ligand-M2+-SO42--H2O, assembly.

Structure-Based Design of Potent and Orally Active Isoindolinone Inhibitors of MDM2-p53 Protein-Protein Interaction

Chessari, Gianni,Hardcastle, Ian R.,Ahn, Jong Sook,Anil, Burcu,Anscombe, Elizabeth,Bawn, Ruth H.,Bevan, Luke D.,Blackburn, Timothy J.,Buck, Ildiko,Cano, Celine,Carbain, Benoit,Castro, Juan,Cons, Ben,Cully, Sarah J.,Endicott, Jane A.,Fazal, Lynsey,Golding, Bernard T.,Griffin, Roger J.,Haggerty, Karen,Harnor, Suzannah J.,Hearn, Keisha,Hobson, Stephen,Holvey, Rhian S.,Howard, Steven,Jennings, Claire E.,Johnson, Christopher N.,Lunec, John,Miller, Duncan C.,Newell, David R.,Noble, Martin E. M.,Reeks, Judith,Revill, Charlotte H.,Riedinger, Christiane,St. Denis, Jeffrey D.,Tamanini, Emiliano,Thomas, Huw,Thompson, Neil T.,Vinkovi?, Mladen,Wedge, Stephen R.,Williams, Pamela A.,Wilsher, Nicola E.,Zhang, Bian,Zhao, Yan

supporting information, p. 4071 - 4088 (2021/05/04)

Inhibition of murine double minute 2 (MDM2)-p53 protein-protein interaction with small molecules has been shown to reactivate p53 and inhibit tumor growth. Here, we describe rational, structure-guided, design of novel isoindolinone-based MDM2 inhibitors. MDM2 X-ray crystallography, quantum mechanics ligand-based design, and metabolite identification all contributed toward the discovery of potent in vitro and in vivo inhibitors of the MDM2-p53 interaction with representative compounds inducing cytostasis in an SJSA-1 osteosarcoma xenograft model following once-daily oral administration.

Unprecedented reductive cyclisation of salophen ligands to tetrahydroquinoxalines during metal complex formation

Dowsett, Mark R.,Lamb, Katie J.,North, Michael,Parker, Rachel R.,Whitwood, Adrian C.

supporting information, p. 4844 - 4847 (2020/05/13)

The synthesis of novel tetrahydroquinoxalines by a metal induced one-electron reductive cyclisation of salophen ligands was found to occur when a salophen ligand was treated with chromium(ii) chloride or decamethylcobaltocene.

Phosphine-Catalyzed [3+2] Annulation of β-Sulfonamido-Substituted Enones with Sulfamate-Derived Cyclic Imines

Shi, Wangyu,Zhou, Leijie,Mao, Biming,Wang, Qijun,Wang, Chang,Zhang, Cheng,Li, Xuefeng,Xiao, Yumei,Guo, Hongchao

supporting information, p. 679 - 685 (2019/01/24)

Phosphine-catalyzed [3+2] annulation of β-sulfonamido-substituted enones and sulfamate-derived cyclic imines has been developed, giving a series of imidazoline derivatives in moderate to excellent yields with good to excellent diastereoselectivities. A scale-up reaction worked well under mild reaction conditions. A possible mechanism was proposed on the basis of the results obtained.

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