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2094-72-6 Usage

Uses

1-Adamantanecarbonyl chloride was used in the preparation of efficient amine-modified oligodeoxynucleotides for fabrication of DNA microarrays.

General Description

1-Adamantanecarbonyl chloride on reaction with triethylammonium isopropylphosphite forms mixed anhydride, an efficient capping reagent for the hydrogen-phosphonate DNA synthesis. It is a good substrate for Friedel–Crafts acylation of anisole in the presence of indium metal.

Check Digit Verification of cas no

The CAS Registry Mumber 2094-72-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,9 and 4 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 2094-72:
(6*2)+(5*0)+(4*9)+(3*4)+(2*7)+(1*2)=76
76 % 10 = 6
So 2094-72-6 is a valid CAS Registry Number.
InChI:InChI=1/C11H15ClO/c12-10(13)11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2

2094-72-6 Well-known Company Product Price

  • Brand
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  • CAS number
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  • Detail
  • Alfa Aesar

  • (L02352)  Adamantane-1-carbonyl chloride, 97%   

  • 2094-72-6

  • 10g

  • 562.0CNY

  • Detail
  • Alfa Aesar

  • (L02352)  Adamantane-1-carbonyl chloride, 97%   

  • 2094-72-6

  • 50g

  • 2003.0CNY

  • Detail
  • Aldrich

  • (117722)  1-Adamantanecarbonylchloride  95%

  • 2094-72-6

  • 117722-5G

  • 258.57CNY

  • Detail
  • Aldrich

  • (117722)  1-Adamantanecarbonylchloride  95%

  • 2094-72-6

  • 117722-25G

  • 916.11CNY

  • Detail

2094-72-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name adamantane-1-carbonyl chloride

1.2 Other means of identification

Product number -
Other names 1-Adamantanecarboxlic acid chloride

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:2094-72-6 SDS

2094-72-6Synthetic route

1-Adamantanecarboxylic acid
828-51-3

1-Adamantanecarboxylic acid

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

Conditions
ConditionsYield
With thionyl chloride at 80℃; for 2h;100%
With oxalyl dichloride; N,N-dimethyl-formamide at 25℃; for 1.5h;100%
With thionyl chloride at 80℃; for 3h;99%
1-Adamantyl bromide
768-90-1

1-Adamantyl bromide

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) magnesium, 1,2-dibromoethane / 1.) diethyl ether, 35 deg C
2: 90 percent / SOCl2 / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / hexane / 5 h / Cooling with ice
2: thionyl chloride / benzene / 5 h / 80 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: magnesium; iodine / diethyl ether / 2 h / Inert atmosphere
1.2: 3.5 h / Inert atmosphere
2.1: thionyl chloride / 1 h / 80 °C
View Scheme
adamantoyltris(trimethylsilyl)germane
104164-53-6

adamantoyltris(trimethylsilyl)germane

A

tris(trimethylsilyl)germyl chloride
104164-55-8

tris(trimethylsilyl)germyl chloride

B

{(CH3)3Si}2Ge{C(OSi(CH3)3)C10H15}

{(CH3)3Si}2Ge{C(OSi(CH3)3)C10H15}

C

chloroform
67-66-3

chloroform

D

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

Conditions
ConditionsYield
In tetrachloromethane byproducts: Me3SiCl, hexachloroethane; Irradiation (UV/VIS); NMR tubes contg. the acylgermane/CCl4 sealed under vac., irradiated (two 100W Hg lamps, λ>360 nm) for up to 3h, with cooling to -15°C), soln. remained colourless; not isolated, detected by NMR-spect.;A >65
B 0%
C <1
D >99
adamantane
281-23-2

adamantane

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: bromine / 6 h / 85 °C
2.1: magnesium; iodine / diethyl ether / 2 h / Inert atmosphere
2.2: 3.5 h / Inert atmosphere
3.1: thionyl chloride / 1 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: bromine / 85 - 110 °C
2: sulfuric acid / tetrahydrofuran / 3 h / 5 - 10 °C
3: thionyl chloride / 2 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: bromine / 85 - 110 °C / Green chemistry
2: sulfuric acid / tetrahydrofuran / 3 h / 5 - 10 °C / Green chemistry
3: thionyl chloride / 2 h / 80 °C / Green chemistry
View Scheme
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

C36H36O6

C36H36O6

Conditions
ConditionsYield
In pyridine for 3h; Ambient temperature;100%
1,3-dipropyl-5,6-diaminouracil
81250-34-2

1,3-dipropyl-5,6-diaminouracil

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

1,3-dipropyl-8-(1-adamantyl)xanthine
127946-26-3

1,3-dipropyl-8-(1-adamantyl)xanthine

Conditions
ConditionsYield
In pyridine100%
7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine
911010-77-0

7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

C25H30N4O
911006-44-5

C25H30N4O

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In chloroform at 160℃; for 0.116667h; Product distribution / selectivity; Microwave irradiation;100%
4-aminobutyrylaldehyde diethylacetal
6346-09-4

4-aminobutyrylaldehyde diethylacetal

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

N-(4,4-diethoxybutyl)adamantane-1-carboxamide
1148156-24-4

N-(4,4-diethoxybutyl)adamantane-1-carboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
(S)-[1,1']-binaphthalenyl-2,2'-diol
18531-99-2

(S)-[1,1']-binaphthalenyl-2,2'-diol

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

(S)-2-adamantanecarbonyloxy-2'-hydroxy-1,1'-binaphthyl

(S)-2-adamantanecarbonyloxy-2'-hydroxy-1,1'-binaphthyl

Conditions
ConditionsYield
With triethylamine In dichloromethane at -10 - 20℃;100%
With dmap; triethylamine In tetrahydrofuran at -5 - 20℃; for 24h; Inert atmosphere;95%
With dmap; triethylamine In tetrahydrofuran at -10 - 20℃; Inert atmosphere;95%
4-phenylpiperidine
771-99-3

4-phenylpiperidine

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

C22H29NO
312504-53-3

C22H29NO

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 0.5h;100%
1-amino-4-[(tert-butyloxycarbonyl)amino]butane
68076-36-8

1-amino-4-[(tert-butyloxycarbonyl)amino]butane

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

N-(4-tert-butoxycarbonylamino)butyl-1-adamantanecarboxamide
1310686-26-0

N-(4-tert-butoxycarbonylamino)butyl-1-adamantanecarboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;100%
3-trifluoromethylaniline
98-16-8

3-trifluoromethylaniline

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

N-[3-(trifluoromethyl)phenyl]adamantane-1-carboxamide
42600-84-0

N-[3-(trifluoromethyl)phenyl]adamantane-1-carboxamide

Conditions
ConditionsYield
With triethylamine In acetone at 90℃; for 3h; Inert atmosphere;100%
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

3-hydroxy-2,2-dimethylpropyl (3r,5r,7r)-adamantane-1-carboxylate

3-hydroxy-2,2-dimethylpropyl (3r,5r,7r)-adamantane-1-carboxylate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;
3(S)-tert-Butoxycarbonylamino-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one
209219-68-1

3(S)-tert-Butoxycarbonylamino-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

2-oxo-3-tert-butoxycarbonylamino-5-(adamantan-1-yl)carbonyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

2-oxo-3-tert-butoxycarbonylamino-5-(adamantan-1-yl)carbonyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Conditions
ConditionsYield
With pyridine In 1,2-dichloro-ethane99.8%
trimethylsilylazide
4648-54-8

trimethylsilylazide

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

1-adamantyl isocyanate
4411-25-0

1-adamantyl isocyanate

Conditions
ConditionsYield
zinc(II) iodide In tetrachloromethane for 6h; Heating;99%
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

Bis(trimethylsilyl)ethyne
14630-40-1

Bis(trimethylsilyl)ethyne

ethynyl adamant-1-yl ketone
94609-13-9

ethynyl adamant-1-yl ketone

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at -20℃; for 1.25h;99%
methyl 3-acetyl-4-hydroxybenzoate
57009-12-8

methyl 3-acetyl-4-hydroxybenzoate

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

adamantane-1-carboxylic acid 2-acetyl-4-(methoxycarbonyl)phenyl ester
750572-54-4

adamantane-1-carboxylic acid 2-acetyl-4-(methoxycarbonyl)phenyl ester

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 18h;99%
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

(3-acetyl-4-hydroxyphenyl)acetic acid methyl ester
145042-91-7

(3-acetyl-4-hydroxyphenyl)acetic acid methyl ester

adamantane-1-carboxylic acid 2-acetyl-4-methoxycarbonylmethylphenyl ester
750572-53-3

adamantane-1-carboxylic acid 2-acetyl-4-methoxycarbonylmethylphenyl ester

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 18h;99%
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

Nα,Nα-bis[(tert-butyloxycarbonyl)methyl]-L-lysine tert-butyl ester
205379-08-4

Nα,Nα-bis[(tert-butyloxycarbonyl)methyl]-L-lysine tert-butyl ester

C33H56N2O7

C33H56N2O7

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;99%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;77%
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

N-[4-chloro-3-(trifluoromethyl)phenyl]adamantane-1-carboxamide

N-[4-chloro-3-(trifluoromethyl)phenyl]adamantane-1-carboxamide

Conditions
ConditionsYield
With triethylamine In acetone at 90℃; for 3h; Inert atmosphere;99%
2,3,4,5,6-pentafluoroaniline
771-60-8

2,3,4,5,6-pentafluoroaniline

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

N-[4-chloro-3-(trifluoromethyl)phenyl]adamantane-1-carboxamide

N-[4-chloro-3-(trifluoromethyl)phenyl]adamantane-1-carboxamide

Conditions
ConditionsYield
With triethylamine In acetone at 90℃; for 3h; Inert atmosphere;99%
(+)-endo-Fenchylamine
131348-06-6

(+)-endo-Fenchylamine

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

N-((1R,2R,4S)-1.3.3-trimethylbicyclo[2.2.1]heptan-2-yl)adamantane-1-carboxamide

N-((1R,2R,4S)-1.3.3-trimethylbicyclo[2.2.1]heptan-2-yl)adamantane-1-carboxamide

Conditions
ConditionsYield
With triethylamine In toluene at 0 - 20℃; for 12h;99%
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

(2R,4S,5R)-1-benzyl-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide

(2R,4S,5R)-1-benzyl-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide

O-1-adamantoyl-N-benzylcinchoninium bromide

O-1-adamantoyl-N-benzylcinchoninium bromide

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane at 20℃; for 0.5h;98.3%
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

A

1-Adamantyl bromide
768-90-1

1-Adamantyl bromide

B

2-<(trichloromethyl)thio>pyridine
66832-24-4

2-<(trichloromethyl)thio>pyridine

Conditions
ConditionsYield
With Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt; dmap at 105℃; for 0.5h;A 98%
B n/a
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

(R)-1-benzyl-3-aminopyrrolidine
114715-39-8

(R)-1-benzyl-3-aminopyrrolidine

(R)-N-(1-Benzylpyrrolidin-3-yl)-1-adamantanecarboxamide
920009-45-6

(R)-N-(1-Benzylpyrrolidin-3-yl)-1-adamantanecarboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane Acylation;98%
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

(3S)-1-benzyl-3-pyrrolidinamine
114715-38-7

(3S)-1-benzyl-3-pyrrolidinamine

(S)-N-(1-benzylpyrrolidin-3-yl)-1-adamantanecarboxamide
267643-71-0

(S)-N-(1-benzylpyrrolidin-3-yl)-1-adamantanecarboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane Acylation;98%
With triethylamine In ethyl acetate; N,N-dimethyl-formamide
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

6-aminohexanoic acid
60-32-2

6-aminohexanoic acid

6-[(Adamantane-1-carbonyl)-amino]-hexanoic acid
34790-40-4

6-[(Adamantane-1-carbonyl)-amino]-hexanoic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 0℃; for 2h;98%
(1S,2R)-(+)-norphedrine
37577-28-9

(1S,2R)-(+)-norphedrine

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)adamantane-1-carboxamide
1050521-37-3

N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)adamantane-1-carboxamide

Conditions
ConditionsYield
Stage #1: (1S,2R)-(+)-norphedrine; 1-Adamantanecarbonyl chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; Cooling with ice;
Stage #2: With sodium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 4h; Alkaline aqueous solution;
98%
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

(S)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol
39648-74-3, 65355-00-2, 65355-14-8

(S)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol

(S)-2-adamantanecarbonyloxy-2'-hydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl

(S)-2-adamantanecarbonyloxy-2'-hydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl

Conditions
ConditionsYield
98%
5-fluoro-N1-[2-(morpholin-4-yl)ethyl]-1,2-phenylenediamine
163618-06-2

5-fluoro-N1-[2-(morpholin-4-yl)ethyl]-1,2-phenylenediamine

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

N-(1-adamantanecarbonyl)-4-fluoro-N'-[2-(morpholin-4-yl)ethyl]-1,2-phenylenediamine
163618-07-3

N-(1-adamantanecarbonyl)-4-fluoro-N'-[2-(morpholin-4-yl)ethyl]-1,2-phenylenediamine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 60℃; for 1.5h;98%
C27H28F3N2O(1+)*Br(1-)

C27H28F3N2O(1+)*Br(1-)

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

O-1-adamantoyl-N-(3-trifluoromethylbenzyl)cinchoninium bromide

O-1-adamantoyl-N-(3-trifluoromethylbenzyl)cinchoninium bromide

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane at 20℃; for 0.5h;98%
quinidium bromide

quinidium bromide

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

O-1-adamantoyl-N-(9-anthracenylmethyl)quinidium bromide

O-1-adamantoyl-N-(9-anthracenylmethyl)quinidium bromide

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane at 20℃; for 0.5h;98%
3-iodoindazole
66607-27-0

3-iodoindazole

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

adamantaneformoxyl-3-iodoindazole

adamantaneformoxyl-3-iodoindazole

Conditions
ConditionsYield
Stage #1: 3-iodoindazole With potassium tert-butylate In tetrahydrofuran at 0℃; for 1h;
Stage #2: 1-Adamantanecarbonyl chloride In tetrahydrofuran at 20℃; for 4h;
98%

2094-72-6Relevant articles and documents

Adamantylated organosilatranes: Design, synthesis, and potential appraisal in surface modification and anti-protozoal activity

Singh, Gurjaspreet,Rani, Sunita,Gawri, Sanchita,Sinha, Shweta,Sehgal, Rakesh

, p. 11626 - 11639 (2017)

The present investigation evaluates the design and facile synthesis of a series of organosilatranes (1-7) tethered with the privileged adamantane motif, labelled as a 'lipophilic bullet', via numerous biocompatible linkages i.e. amide, ester, thioester, urea, thiourea, and thiocarbamate groups. The assembled silatranes have been scrupulously characterized by elemental analysis, FT-IR and NMR (1H and 13C) spectroscopy, and mass spectrometry. The parasitic diseases caused by unicellular protozoa, Giardia lamblia (G. lamblia) and Trichomonas vaginalis (T. vaginalis), represent a major health burden, therefore the synthesized compounds were probed for in vitro giardicidal and trichomonacidal activities. With this aim, firstly the pharmacokinetic profiles of the compounds were scrutinized using absorption, distribution, metabolism, excretion, and toxicity (ADMET) tools and on the whole, all compounds showed good oral bioavailability. The anti-parasitic activity of the newly synthesized compounds was evaluated in comparison to a standard drug (metronidazole) by 3-(4,5-dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT) assay. All the compounds displayed significant activity against G. lamblia and T. vaginalis with IC50 values ranging from 10.9-127.4 μM and 6.2-128.9 μM, respectively. To improve the aqueous solubility of the synthesized compounds, the enticing feature of the adamantane moiety to undergo inclusion binding with the β-cyclodextrin cavity is explored. Furthermore, a simplistic methodology is proposed to covalently anchor adamantylated silatrane onto the surface of magnetic silica nanoparticles. This material promises to be a non-invasive and externally controlled drug delivery system with enormous anti-protozoal potential.

-

Razuvajev et al.

, p. 4925,4929 (1969)

-

A novel self-healing power cable insulating material based on host-guest interactions

Peng, Lei,Zhang, Manjun,Lin, Musong,Fu, Qiang

, p. 25313 - 25318 (2018)

The insulating materials used in power cables are susceptible to damage and cracks during installation and operation. To solve this problem, we have prepared a self-healing material PVP/p(HEMA-co-BA), which is synthesized by radical polymerization using HEMA, BA, PVP and a host-guest assembly. The host-guest assembly is constructed through interactions between host and guest molecules (CD-Al2O3 NPs act as the host, and HEMA-Ad acts as the guest). The characterization results of the materials show that there are two kinds of supramolecular interactions, namely, the host-guest interaction and the hydrogen bonding. The material possesses good thermal stability (heat-resisting temperature can reach 200 °C) and good electrical performance. The storage modulus of the material can be increased up to 432 MPa using a cross-linking agent at 20 °C. Furthermore, the material exhibits self-healing property, and it can self-heal several times; its self-healing efficiency is relative to the dosage of the cross-linking agent.

Mannich bases of 1,2,4-triazole-3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies

Milo?ev, Milorad Z.,Jakovljevi?, Katarina,Joksovi?, Milan D.,Stanojkovi?, Tatjana,Mati?, Ivana Z.,Perovi?, Milka,Te?i?, Vesna,Kanazir, Selma,Mladenovi?, Milan,Rodi?, Marko V.,Leovac, Vukadin M.,Trifunovi?, Sne?ana,Markovi?, Violeta

, p. 943 - 952 (2017)

A series of 18 novel N-Mannich bases derived from 5-adamantyl-1,2,4-triazole-3-thione was synthesized and characterized using NMR spectroscopy and X-ray diffraction technique. All derivatives were evaluated for their anticancer potential against four human cancer cell lines. Several tested compounds exerted good cytotoxic activities on K562 and HL-60 cell lines, along with pronounced selectivity, showing lower cytotoxicity against normal fibroblasts MRC-5 compared to cancer cells. The effects of compounds 5b, 5e, and 5j on the cell cycle were investigated by flow cytometric analysis. It was found that these compounds cause the accumulation of cells in the subG1 and G1 phases of the cell cycle and induce caspase-dependent apoptosis, while the anti-angiogenic effects of 5b, 5e, and 5j have been confirmed in EA.hy926 cells using a tube formation assay. Further, the interaction of Bax protein with compound 5b was investigated by means of molecular modeling, applying the combined molecular docking/molecular dynamics approach.

Synthesis, X-ray, Hirshfeld surface analysis, exploration of DNA binding, urease enzyme inhibition and anticancer activities of novel adamantane-naphthyl thiourea conjugate

Arshad, Nasima,Saeed, Aamer,Perveen, Fouzia,Ujan, Rabail,Farooqi, Shahid I.,Ali Channar, Pervaiz,Shabir, Ghulam,El-Seedi, Hesham R.,Javed, Aneela,Yamin, Maham,Bolte, Michael,H?kelek, Tuncer

, (2021)

1-(adamantane-1-carbonyl-3-(1-naphthyl)) thiourea (C22H24N2OS (4), was synthesized by the reaction of freshly prepared adamantane-1-carbonyl chloride from corresponding acid (3) with ammonium thiocyanate in 1:1 M ratio in dry acetone to afford the adamantane-1-carbonyl isothiocyanate (2) in situ followed by treatment with 1-naphthyl amine (3). The structure was established by elemental analyses, FTIR, 1H, 13C NMR and mass spectroscopy. The molecular and crystal structure were determined by single crystal X-ray analysis. It belongs to triclinic system P ? 1 space group with a = 6.7832(5) ?, b = 11.1810(8) ?, c = 13.6660(10) ?, α = 105.941(6)°, β = 103.730(6)°, γ = 104.562(6)°, Z = 2, V = 910.82(11) ?3. The naphthyl group is almost planar. In the crystal structure, intermolecular C[sbnd]H···O hydrogen bonds link the molecules into centrosymmetric dimers, enclosing R22(14) ring motifs, while the intramolecular N[sbnd]H···O hydrogen bonds enclose S(6) ring motifs, in which they may be effective in the stabilization of the structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H … H (59.3%), H … C/C … H (19.8%) and H … S/S … H (10.1%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. DFT, molecular docking and urease inhibition studies revealed stability and electron withdrawing nature of 4 as compared to DNA base pairs and residues of urease. The DNA binding results from docking, UV– visible spectroscopy, and viscosity studies indicated significant binding of 4 with the DNA via intercalation and groove binding. Further investigation of the compound was done on hepatocellular carcinoma; Huh-7 cell line as well as normal human embryonic kidney; Hek-293 cell line. The compound showed significant cytotoxic activity against Huh-7 cells in comparison to normal Hek-293 cells indicating selective cytotoxicity towards cancer cells.

Conductive Elastomers with Autonomic Self-Healing Properties

Guo, Kun,Zhang, Da-Li,Zhang, Xiao-Mei,Zhang, Jian,Ding, Li-Sheng,Li, Bang-Jing,Zhang, Sheng

, p. 12127 - 12133 (2015)

Healable, electrically conductive materials are highly desirable and valuable for the development of various modern electronics. But the preparation of a material combining good mechanical elasticity, functional properties, and intrinsic self-healing ability remains a great challenge. Here, we design composites by connecting a polymer network and single-walled carbon nanotubes (SWCNTs) through host-guest interactions. The resulting materials show bulk electrical conductivity, proximity sensitivity, humidity sensitivity and are able to self-heal without external stimulus under ambient conditions rapidly. Furthermore, they also possess elasticity comparable to commercial rubbers.

Directed C?H Bond Oxidation of Bridged Cycloalkanes Catalyzed by Palladium(II) Acetate

Larrosa, Marta,Zonker, Benjamin,Volkmann, Jannis,Wech, Felix,Logemann, Christian,Hausmann, Heike,Hrdina, Radim

, p. 6269 - 6276 (2018)

We have developed a synthesis of 1,2-substituted adamantane carboxylic acids and further bridged cycloalkanes (cage compounds) by palladium acetate-catalyzed C?H bond oxidation. Acetoxylation of cycloalkane framework was performed using picolylamide as a directing group. Modification of the substrate, ligand design and variation of reaction conditions enabled us to study the mechanism of acetoxylation of aliphatic compounds. Post-functionalization reactions and cleavage of the directing group were developed. For the first time the synthesis and characterization of a β-C3-tri-substituted adamantane derivatives was achieved.

Activation of Sirtuin 2 Inhibitors Employing Photoswitchable Geometry and Aqueous Solubility

Grathwol, Christoph W.,W?ssner, Nathalie,Behnisch-Cornwell, Steven,Schulig, Lukas,Zhang, Lin,Einsle, Oliver,Jung, Manfred,Link, Andreas

, p. 1480 - 1489 (2020)

Because isoenzymes of the experimentally and therapeutically extremely relevant sirtuin family show high similarity, addressing the unique selectivity pocket of sirtuin 2 is a promising strategy towards selective inhibitors. An unrelated approach towards selective inhibition of isoenzymes with varied tissue distribution is targeted drug delivery or spatiotemporal activation by photochemical activation. Azologization of two nicotinamide-mimicking lead structures was undertaken to combine both approaches and yielded a set of 33 azobenzenes and azopyridines that have been evaluated for their photochemical behaviour and bioactivity. For some compounds, inhibitory activity reached the sub-micromolar range in their thermodynamically favoured E form and could be decreased by photoisomerization to the metastable Z form. Besides, derivatization with long-chain fatty acids yielded potent sirtuin 2 inhibitors, featuring another intriguing aspect of azo-based photoswitches. In these compounds, switching to the Z isomer increased aqueous solubility and thereby enhanced biological activity by up to a factor of 21. The biological activity of two compounds was confirmed by hyperacetylation of sirtuin specific histone proteins in a cell-based activity assay.

Fluorous 1,2,3-Triazol-4-ylmethyl Amines and Amine Derivatives for Novel Surfactant Applications

Francis, Dominic V.,Harper, Jason B.,Read, Roger W.

, p. 57 - 68 (2015)

A series of fluorous surfactants with additional functionality were generated through the attachment of substituents at the amino nitrogen atom of the surfactant moiety. Examples of molecules containing one and two triazole ring systems were synthesized through N-alkylation and N-acylation strategies.

Structural Basis of Nanomolar Inhibition of Tumor-Associated Carbonic Anhydrase IX: X-Ray Crystallographic and Inhibition Study of Lipophilic Inhibitors with Acetazolamide Backbone

Andring, Jacob T.,Fouch, Mallorie,Akocak, Suleyman,Angeli, Andrea,Supuran, Claudiu T.,Ilies, Marc A.,McKenna, Robert

, p. 13064 - 13075 (2020/11/20)

This study provides a structure-Activity relationship study of a series of lipophilic carbonic anhydrase (CA) inhibitors with an acetazolamide backbone. The inhibitors were tested against the tumor-expressed CA isozyme IX (CA IX), and the cytosolic CA I, CA II, and membrane-bound CA IV. The study identified several low nanomolar potent inhibitors against CA IX, with lipophilicities spanning two log units. Very potent pan-inhibitors with nanomolar potency against CA IX and sub-nanomolar potency against CA II and CA IV, and with potency against CA I one order of magnitude better than the parent acetazolamide 1 were also identified in this study, together with compounds that displayed selectivity against membrane-bound CA IV. A comprehensive X-ray crystallographic study (12 crystal structures), involving both CA II and a soluble CA IX mimetic (CA IX-mimic), revealed the structural basis of this particular inhibition profile and laid the foundation for further developments toward more potent and selective inhibitors for the tumor-expressed CA IX.

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