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4-Chlorophenyl isocyanate is a colorless to yellow liquid or crystalline solid that serves as an intermediate in the manufacturing of pesticides and pharmaceuticals. It is a white to yellow crystalline solid with chemical properties that make it suitable for various applications in different industries.

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  • 104-12-1 Structure
  • Basic information

    1. Product Name: 4-Chlorophenyl isocyanate
    2. Synonyms: 1-chloro-4-isocyanato-benzen;1-Chloro-4-isocyanatobenzene;1-Chloro-4-isocyanato-benzene;4-chloroisocyanatobenzene;4-Chloro-iso-cyanatobenzene;4-Chlorphenylisocyanate;benzene,1-chloro-4-isocyanato;benzene,1-chloro-4-isocyanato-
    3. CAS NO:104-12-1
    4. Molecular Formula: C7H4ClNO
    5. Molecular Weight: 153.57
    6. EINECS: 203-176-9
    7. Product Categories: organic chemical;Building Blocks;Chemical Synthesis;Isocyanates;Nitrogen Compounds;Organic Building Blocks
    8. Mol File: 104-12-1.mol
  • Chemical Properties

    1. Melting Point: 26-29 °C(lit.)
    2. Boiling Point: 203-204 °C(lit.)
    3. Flash Point: >230 °F
    4. Appearance: White to yellow/Crystalline Solid
    5. Density: 1.2 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.226mmHg at 25°C
    7. Refractive Index: n20/D 1.5618(lit.)
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. Water Solubility: DECOMPOSES
    11. Sensitive: Moisture Sensitive/Lachrymatory
    12. BRN: 386235
    13. CAS DataBase Reference: 4-Chlorophenyl isocyanate(CAS DataBase Reference)
    14. NIST Chemistry Reference: 4-Chlorophenyl isocyanate(104-12-1)
    15. EPA Substance Registry System: 4-Chlorophenyl isocyanate(104-12-1)
  • Safety Data

    1. Hazard Codes: T+,T,C
    2. Statements: 25-26-37/38-41-42-52/53
    3. Safety Statements: 23-26-28-36/37/39-45-61-38-37/39-28A-22
    4. RIDADR: UN 2811 6.1/PG 2
    5. WGK Germany: 3
    6. RTECS: NQ8575000
    7. F: 10-19-21
    8. TSCA: Yes
    9. HazardClass: 6.1
    10. PackingGroup: II
    11. Hazardous Substances Data: 104-12-1(Hazardous Substances Data)

104-12-1 Usage

Uses

Used in Chemical Synthesis:
4-Chlorophenyl isocyanate is used as a chemical intermediate for the preparation of isothiocyanates. It plays a crucial role in the synthesis of various compounds, contributing to the development of new products in the chemical industry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Chlorophenyl isocyanate is used as a key intermediate in the synthesis of various drugs. Its ability to undergo [2+2] cycloaddition reactions with dihydrofuran to give bicyclic δ-lactams in high yield makes it a valuable component in the development of new pharmaceutical compounds.
Used in Pesticide Industry:
4-Chlorophenyl isocyanate is also utilized in the preparation of pesticides. Its role as an intermediate allows for the creation of effective pest control solutions, contributing to the agricultural industry's efforts to protect crops and maintain food security.

Synthesis Reference(s)

The Journal of Organic Chemistry, 34, p. 3200, 1969 DOI: 10.1021/jo01262a089

Reactivity Profile

Isocyanates and thioisocyanates are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].

Safety Profile

Poison by ingestion and inhalation. Unspecified human systemic effects. A severe eye and moderate skin irritant. A flammable liquid when exposed to heat or flame. Dangerous, can explode on distillation. When heated to decomposition it emits toxic fumes of Cl-, CN-, and NOx.

Purification Methods

Purify the isocyanate by recrystallisation from pet ether (b 30-40o) or better by fractional distillation. TOXIC irritant. [Beilstein 12 H 616, 12 III 1376, 12 IV 1213.]

Check Digit Verification of cas no

The CAS Registry Mumber 104-12-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 104-12:
(5*1)+(4*0)+(3*4)+(2*1)+(1*2)=21
21 % 10 = 1
So 104-12-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H4ClNO/c7-5-1-3-6(8-9)4-2-5/h1-4H

104-12-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A14966)  4-Chlorophenyl isocyanate, 98%   

  • 104-12-1

  • 5g

  • 185.0CNY

  • Detail
  • Alfa Aesar

  • (A14966)  4-Chlorophenyl isocyanate, 98%   

  • 104-12-1

  • 25g

  • 238.0CNY

  • Detail
  • Alfa Aesar

  • (A14966)  4-Chlorophenyl isocyanate, 98%   

  • 104-12-1

  • 100g

  • 359.0CNY

  • Detail
  • Aldrich

  • (152277)  4-Chlorophenylisocyanate  98%

  • 104-12-1

  • 152277-5G

  • 253.89CNY

  • Detail
  • Aldrich

  • (152277)  4-Chlorophenylisocyanate  98%

  • 104-12-1

  • 152277-100G

  • 1,083.42CNY

  • Detail

104-12-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Chlorophenyl Isocyanate

1.2 Other means of identification

Product number -
Other names 4-Chlorophenyl isocyanate

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:104-12-1 SDS

104-12-1Synthetic route

carbon dioxide
124-38-9

carbon dioxide

N-p-chlorophenyltriphenylphosphinimine
31641-65-3

N-p-chlorophenyltriphenylphosphinimine

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
In benzene for 2h; Heating;97%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

4-chloro-aniline
106-47-8

4-chloro-aniline

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
In ethyl acetate at 0 - 5℃; for 3h; Solvent; Cooling with ice; Reflux;92%
In 1,2-dichloro-ethane at 70 - 83℃;89.4%
Stage #1: bis(trichloromethyl) carbonate; 4-chloro-aniline In dichloromethane at 20℃; for 0.5h;
Stage #2: With triethylamine In dichloromethane at -35 - 20℃; for 2h;
84%
Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

N-(4-chlorophenyl)thiomorpholine-4-carboxamide 1,1-dioxide

N-(4-chlorophenyl)thiomorpholine-4-carboxamide 1,1-dioxide

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 3h;77.1%
(2S,3S)-1-(4-Chloro-phenyl)-3-methyl-4-oxo-azetidine-2-carbaldehyde

(2S,3S)-1-(4-Chloro-phenyl)-3-methyl-4-oxo-azetidine-2-carbaldehyde

A

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

B

[(Z)-4-Chloro-phenylimino]-acetaldehyde

[(Z)-4-Chloro-phenylimino]-acetaldehyde

Conditions
ConditionsYield
at 550℃; under 0.002 Torr;A 8%
B 77%
4-chlorobenzoyl azide
21368-28-5

4-chlorobenzoyl azide

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
In toluene for 1.5h; Heating;75%
In toluene at 100℃; for 1h; Reflux;
Curtius Rearrangement;
1-methoxy-2-methylprop-1-ene
17574-84-4

1-methoxy-2-methylprop-1-ene

4-chloro-N-(dimethyl-λ4-sulfanylidene)benzamide
36176-95-1

4-chloro-N-(dimethyl-λ4-sulfanylidene)benzamide

A

4,4-dimethyl-5-methoxy-2-(4-chlorophenyl)-2-oxazoline
54573-19-2

4,4-dimethyl-5-methoxy-2-(4-chlorophenyl)-2-oxazoline

B

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

C

4-chlorobenzamide
619-56-7

4-chlorobenzamide

Conditions
ConditionsYield
In benzene at 35℃; for 1h; Mechanism; Product distribution; Irradiation; other temperatures, other solvents, other concentration of reactant;A 49%
B n/a
C n/a
carbon monoxide
201230-82-2

carbon monoxide

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With di(rhodium)tetracarbonyl dichloride; pyridine hydrochloride In chlorobenzene at 185℃; under 38000 Torr; for 1h;49%
bis(tetrahydrofurane)oxovanadium(IV) dichloride; (Bu4N) In 1,2-dichloro-benzene at 120℃; under 750.06 Torr;18%
bis(tetrahydrofurane)oxovanadium(IV) dichloride; (Bu4N) In 1,2-dichloro-benzene at 120℃; under 750.06 Torr; Rate constant;18%
With pyridine; di(rhodium)tetracarbonyl dichloride; pyridine hydrochloride In chlorobenzene at 205℃; under 50 Torr; for 0.666667h; Yield given;
2-((4-chlorophenyl)-amino)-2-oxoacetic acid
17738-71-5

2-((4-chlorophenyl)-amino)-2-oxoacetic acid

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate; copper(II) sulfate In dichloromethane; water at 40℃; for 3h;46%
With ammonium peroxydisulfate; copper diacetate; silver nitrate In dichloromethane; water at 40℃; for 3h;46%
1-methoxy-2-methylprop-1-ene
17574-84-4

1-methoxy-2-methylprop-1-ene

3-(4-chlorophenyl)-1,4,2-dioxazol-5-one
132401-91-3

3-(4-chlorophenyl)-1,4,2-dioxazol-5-one

A

4,4-dimethyl-5-methoxy-2-(4-chlorophenyl)-2-oxazoline
54573-19-2

4,4-dimethyl-5-methoxy-2-(4-chlorophenyl)-2-oxazoline

B

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
In dichloromethane Irradiation;A 9%
B 42%
3-(4-chlorophenyl)-1,4,2-dioxazol-5-one
132401-91-3

3-(4-chlorophenyl)-1,4,2-dioxazol-5-one

A

4,4-dimethyl-5-methoxy-2-(4-chlorophenyl)-2-oxazoline
54573-19-2

4,4-dimethyl-5-methoxy-2-(4-chlorophenyl)-2-oxazoline

B

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With 1-methoxy-2-methylprop-1-ene In dichloromethane Irradiation;A 9%
B 42%
cis-1-(p-chlorophenyl)-4-cyano-3-methylazetidin-2-one

cis-1-(p-chlorophenyl)-4-cyano-3-methylazetidin-2-one

A

(Z)-2-butenenitrile
1190-76-7

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

C

(p-chlorophenyl)iminoacetonitrile
1204614-45-8

(p-chlorophenyl)iminoacetonitrile

D

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
at 720℃; under 0.0015 Torr; regioselective reaction;A n/a
B n/a
C 30%
D n/a
phosgene
75-44-5

phosgene

4-chloro-aniline
106-47-8

4-chloro-aniline

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

phenyl isocyanate
103-71-9

phenyl isocyanate

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With chlorine; 1,1,2,2-tetrachloroethane Erwaermen des Reaktionsprodukts auf 90grad;
phosgene
75-44-5

phosgene

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

A

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

B

4-ethoxyphenyl isocyanate
32459-62-4

4-ethoxyphenyl isocyanate

Conditions
ConditionsYield
With 1-Chloronaphthalene at 240℃;
4-chloro-N-(2,2-diphenylvinylidene)aniline
17205-60-6

4-chloro-N-(2,2-diphenylvinylidene)aniline

A

benzophenone
119-61-9

benzophenone

B

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

C

(4-Chloro-phenyl)-methylidyne-ammonium

(4-Chloro-phenyl)-methylidyne-ammonium

Conditions
ConditionsYield
With oxygen; copper dichloride In N,N-dimethyl-formamide; benzene at 28℃; Mechanism; Rate constant; k=6.1E-2 min-3;
monuron
150-68-5

monuron

A

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

B

dimethyl amine
124-40-3

dimethyl amine

Conditions
ConditionsYield
at 180 - 220℃; Thermodynamic data; ΔH; heat of dissociation;
4-chloro-aniline
106-47-8

4-chloro-aniline

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
In 1,4-dioxane Heating;
With pyrographite In ethyl acetate Heating;
3-Methyl-pyrazole-1-carboxylic acid (4-chloro-phenyl)-amide
69413-36-1

3-Methyl-pyrazole-1-carboxylic acid (4-chloro-phenyl)-amide

A

3-Methylpyrazole
1453-58-3

3-Methylpyrazole

B

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With dibutylamine In tetrachloromethane at 40℃; Rate constant;
In 1,4-dioxane at 40℃; Rate constant; var. aprotic solvents;
O-cyclododecyl-N-(4-chlorophenyl)selenocarbamate
154592-65-1

O-cyclododecyl-N-(4-chlorophenyl)selenocarbamate

A

cis-cyclododecene
1129-89-1

cis-cyclododecene

B

(E)-Cyclododecen
1486-75-5

(E)-Cyclododecen

C

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform-d1 at 80℃; for 4h; Product distribution; rates of olefin at various temperature and time;
N-(4-chlorophenyl)selenocarbamate of cholestanol
154592-71-9

N-(4-chlorophenyl)selenocarbamate of cholestanol

A

5α-cholest-3-ene
28338-69-4

5α-cholest-3-ene

C

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform-d1 at 80℃; for 4h; Product distribution; rates of olefin formation at various temperature and time;
C31H27NP2*C7H5Cl2NNiO

C31H27NP2*C7H5Cl2NNiO

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With copper dichloride In tetrahydrofuran for 0.5h;
N-(4-chlorobenzoyl)-9,10-dihydro-9,10-dimethyl-9,10-epoxyiminoanthracene
58696-04-1

N-(4-chlorobenzoyl)-9,10-dihydro-9,10-dimethyl-9,10-epoxyiminoanthracene

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With triphenylphosphine In benzene Heating;92 % Chromat.
(4-chlorophenyl)carbamic chloride
22536-57-8

(4-chlorophenyl)carbamic chloride

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane; toluene for 0.25h;
phenyl isocyanate
103-71-9

phenyl isocyanate

1,1,2,2-tetrachloroethane
79-34-5

1,1,2,2-tetrachloroethane

chlorine <1 mol>

chlorine <1 mol>

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

chlorine
7782-50-5

chlorine

phenyl isocyanate
103-71-9

phenyl isocyanate

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

A

2,4-dichlorophenyl isocyanate
2612-57-9

2,4-dichlorophenyl isocyanate

B

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

C

2,4,6-trichlorophenyl isocyanate
2505-31-9

2,4,6-trichlorophenyl isocyanate

Conditions
ConditionsYield
at 120 - 130℃;
(4-chloro-phenyl)-carbamic acid methyl ester
940-36-3

(4-chloro-phenyl)-carbamic acid methyl ester

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With montmorillonite K-10 In 1,2-dichloro-benzene at 183℃; for 5h;99 % Chromat.
p-chlorophenyl isocyanide
1885-81-0

p-chlorophenyl isocyanide

A

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

B

4-chloro-aniline
106-47-8

4-chloro-aniline

Conditions
ConditionsYield
With di-tert-butyl peroxide at 56.84℃; for 4.5h; Photolysis;
4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With sodium azide In toluene for 1h; Heating;
Multi-step reaction with 2 steps
1: sodium azide / acetone / 0.5 h / 0 °C
2: toluene / 1 h / 100 °C / Reflux
View Scheme
Stage #1: 4-chloro-benzoyl chloride With sodium azide In water; acetone at 0℃; Curtius Rearrangement;
Stage #2: In toluene for 2h; Curtius Rearrangement; Reflux; Inert atmosphere;
400 mg
[(benzoyl)(4-chlorophenylcarbamoyl)methylene]triphenylphosphorane

[(benzoyl)(4-chlorophenylcarbamoyl)methylene]triphenylphosphorane

A

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

B

(Benzoylmethylene)triphenylphosphorane
20913-05-7

(Benzoylmethylene)triphenylphosphorane

Conditions
ConditionsYield
at 385.25 - 424.85℃; Kinetics;
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

3-(4-Chloro-phenyl)-hexahydro-benzooxazol-2-one
109632-68-0

3-(4-Chloro-phenyl)-hexahydro-benzooxazol-2-one

Conditions
ConditionsYield
Ph4SbI-Bu3SnI In benzene at 80℃; for 2h;100%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

2,4-diaminophanyl diphenylphosphinodithioate

2,4-diaminophanyl diphenylphosphinodithioate

Diphenyl-phosphinodithioic acid 2,4-bis-[3-(4-chloro-phenyl)-ureido]-phenyl ester

Diphenyl-phosphinodithioic acid 2,4-bis-[3-(4-chloro-phenyl)-ureido]-phenyl ester

Conditions
ConditionsYield
In benzene100%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

6,7-dimethoxy-4-(1-piperazinyl)quinazoline
21584-72-5

6,7-dimethoxy-4-(1-piperazinyl)quinazoline

N-(4-Chlorophenyl)-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinecarboxamide

N-(4-Chlorophenyl)-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinecarboxamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;100%
(1R,2S)-2-{[(3aR,4R,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexylamine dihydrochloride

(1R,2S)-2-{[(3aR,4R,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexylamine dihydrochloride

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

N-(4-chlorophenyl)-N'-((1R,2S)-2-{[(3aR,4R,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)urea

N-(4-chlorophenyl)-N'-((1R,2S)-2-{[(3aR,4R,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)urea

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 4.5h;100%
(R)-2-amino-N-[4-(3-oxo-morpholin-4-yl)-phenyl]-3-(dimethoxy-phosphoryl)-propionamide

(R)-2-amino-N-[4-(3-oxo-morpholin-4-yl)-phenyl]-3-(dimethoxy-phosphoryl)-propionamide

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

(R)-2-[3-(4-chlorophenyl)-ureido]-N-[4-(3-oxo-morpholin-4-yl)-phenyl]-3-(dimethoxy-phosphoryl)-propionamide

(R)-2-[3-(4-chlorophenyl)-ureido]-N-[4-(3-oxo-morpholin-4-yl)-phenyl]-3-(dimethoxy-phosphoryl)-propionamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h;100%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

DL-3,4-Dehydroproline
3395-35-5

DL-3,4-Dehydroproline

1-(4-chloro-phenylcarbamoyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid

1-(4-chloro-phenylcarbamoyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate at 80℃; for 16h;100%
2-(adamantan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one
1224513-21-6

2-(adamantan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

N-(4-chlorophenyl)-4,4-dimethyl-3-oxo-2-(adamantan-2-yl)-1,2-diazetidine-1-carboxamide
1224513-00-1

N-(4-chlorophenyl)-4,4-dimethyl-3-oxo-2-(adamantan-2-yl)-1,2-diazetidine-1-carboxamide

Conditions
ConditionsYield
With triethylamine; dmap In dichloromethane at 20℃; for 1.5h;100%
2-fluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenylamine
1231892-80-0

2-fluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenylamine

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

1-[2-fluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(4-chlorophenyl)-urea
1400220-48-5

1-[2-fluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(4-chlorophenyl)-urea

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 23h; Inert atmosphere;100%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

1-t-Butoxycarbonylpiperazine
57260-71-6

1-t-Butoxycarbonylpiperazine

tert-butyl 4-(4-chlorophenylcarbamoyl)piperazine-1-carboxylic acid ester
1315592-03-0

tert-butyl 4-(4-chlorophenylcarbamoyl)piperazine-1-carboxylic acid ester

Conditions
ConditionsYield
In diethyl ether at 20℃; for 3h;99.9%
In dichloromethane at 0 - 20℃; for 1h;89%
In chloroform at 20℃;
In dichloromethane at 20℃; for 2h;
C19H17NO3S
1449770-04-0

C19H17NO3S

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

1-(4-chlorophenyl)-3a-phenyl-3-tosyl-3,3a,7,7a-tetrahydro-1H-benzo[d]imidazole-2,6-dione

1-(4-chlorophenyl)-3a-phenyl-3-tosyl-3,3a,7,7a-tetrahydro-1H-benzo[d]imidazole-2,6-dione

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 25℃; for 0.166667h; diastereoselective reaction;99.5%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

dimethyl amine
124-40-3

dimethyl amine

monuron
150-68-5

monuron

Conditions
ConditionsYield
In chlorobenzene99%
In toluene at 80℃; for 1h;96%
In water; toluene for 2h; Heating;90%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

diethylamine
109-89-7

diethylamine

N,N-diethyl-N'-(4-chlorophenyl)urea
15737-37-8

N,N-diethyl-N'-(4-chlorophenyl)urea

Conditions
ConditionsYield
With [{Ph2P(Se)NCH2CH2NPPh2(Se)}Ti(NMe2)2] In toluene at 25℃; for 1h; Schlenk technique; Inert atmosphere; Glovebox;99%
With [κ2-{(Ph2P-(=Se))}2NCH2(C5H4N)ZnCl2] In toluene at 25℃; Schlenk technique; Inert atmosphere;96%
In benzene for 0.5h;69%
In ethanol
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

1,3,5-tris-(4-chloro-phenyl)-[1,3,5]triazinane-2,4,6-trione
1784-98-1

1,3,5-tris-(4-chloro-phenyl)-[1,3,5]triazinane-2,4,6-trione

Conditions
ConditionsYield
With [(CH2)2N[(CH2)3N[(CH2)3NHC(O)]2]2]2-azidophosphine dendrimer at 20℃; for 5h;99%
With 1,3-diisopropyl-3,4,5,6-tetrahydropyrimidin-1-ium-2-carboxylate In tetrahydrofuran at 75℃; for 1h;99%
With C47H79N4Si3Y In tetrahydrofuran at 23℃; for 12h; Glovebox; Schlenk technique; Inert atmosphere;99%
[(2S,3R)-3-(4-Nitro-phenyl)-aziridin-2-yl]-phenyl-methanone
51659-22-4, 76336-95-3

[(2S,3R)-3-(4-Nitro-phenyl)-aziridin-2-yl]-phenyl-methanone

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

1-(4-Chlorphenylcarbamoyl)-2-(4-nitrophenyl)-3-benzoylaziridin
109831-10-9

1-(4-Chlorphenylcarbamoyl)-2-(4-nitrophenyl)-3-benzoylaziridin

Conditions
ConditionsYield
In diethyl ether for 0.333333h; Heating;99%
6-(methylamino)hexanoic acid
26410-96-8

6-(methylamino)hexanoic acid

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

1-(5-carboxypentyl)-3-(4-chlorophenyl)-1-methylurea

1-(5-carboxypentyl)-3-(4-chlorophenyl)-1-methylurea

Conditions
ConditionsYield
With sodium hydroxide Ambient temperature;99%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
In tetrahydrofuran for 1h; Ambient temperature;99%
2-isopropylidenehydrazino-2,6-dioxo-4,4-dimethylcyclohexyl thioketone
128797-69-3

2-isopropylidenehydrazino-2,6-dioxo-4,4-dimethylcyclohexyl thioketone

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

5-(4,4-Dimethyl-2,6-dioxo-cyclohexylidene)-2,2-dimethyl-[1,3,4]thiadiazolidine-3-carboxylic acid (4-chloro-phenyl)-amide
128797-70-6

5-(4,4-Dimethyl-2,6-dioxo-cyclohexylidene)-2,2-dimethyl-[1,3,4]thiadiazolidine-3-carboxylic acid (4-chloro-phenyl)-amide

Conditions
ConditionsYield
In chloroform for 15h; Ambient temperature;99%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

D-glucosamine hydrochloride
14131-62-5

D-glucosamine hydrochloride

2-<3-(4-chlorophenylureido)>-2-deoxy-α-D-glucopyranose
149117-40-8

2-<3-(4-chlorophenylureido)>-2-deoxy-α-D-glucopyranose

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water for 0.5h; Ambient temperature;99%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

N-benzylaminomethyl-dimethylphosphine oxide
97578-20-6

N-benzylaminomethyl-dimethylphosphine oxide

1-(4-chlorophenyl)-3-benzyl-3-(dimethylphosphinylmethyl)urea

1-(4-chlorophenyl)-3-benzyl-3-(dimethylphosphinylmethyl)urea

Conditions
ConditionsYield
In dichloromethane99%
6-amino-4H-1-benzopyran-4-one
98589-40-3

6-amino-4H-1-benzopyran-4-one

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

1-(4-chloro-phenyl)-3-(4-oxo-4H-chromen-6-yl)-urea
839714-64-6

1-(4-chloro-phenyl)-3-(4-oxo-4H-chromen-6-yl)-urea

Conditions
ConditionsYield
In toluene at 80℃; for 18h; Heating / reflux;99%
In toluene at 80℃; for 18h; Heating / reflux;99%
((CH3)5C5)Ru(P(CH3)3)2(Si(C6H5)2)(1+)*B(C6F5)4(1-)=[((CH3)5C5)Ru(P(CH3)3)2(Si(C6H5)2)][B(C6F5)4]

((CH3)5C5)Ru(P(CH3)3)2(Si(C6H5)2)(1+)*B(C6F5)4(1-)=[((CH3)5C5)Ru(P(CH3)3)2(Si(C6H5)2)][B(C6F5)4]

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

C5(CH3)5(P(CH3)3)2RuSi(C6H5)2N(ClC6H4)CO(1+)*B(C6F5)4(1-)=[C5(CH3)5(P(CH3)3)2RuSi(C6H5)2N(ClC6H4)CO]B(C6F5)4
198082-74-5

C5(CH3)5(P(CH3)3)2RuSi(C6H5)2N(ClC6H4)CO(1+)*B(C6F5)4(1-)=[C5(CH3)5(P(CH3)3)2RuSi(C6H5)2N(ClC6H4)CO]B(C6F5)4

Conditions
ConditionsYield
In dichloromethane-d2 inert atmosphere; not isolated;99%
5-amino-1,3-dihydro-2H-indol-2-one
20876-36-2

5-amino-1,3-dihydro-2H-indol-2-one

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

1-(4-chlorophenyl)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)-urea
1171584-41-0

1-(4-chlorophenyl)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)-urea

Conditions
ConditionsYield
In methanol; dichloromethane at 10 - 20℃;99%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

diphenylphosphane
829-85-6

diphenylphosphane

N-(4-chlorophenyl)-1,1-diphenylphosphanecarboxamide
1410203-07-4

N-(4-chlorophenyl)-1,1-diphenylphosphanecarboxamide

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 3h; Schlenk technique; Inert atmosphere;99%
With Zr(tBu-ONNMe2O)Bn2; trityl tetrakis(pentafluorophenyl)borate In chlorobenzene at 60℃; for 24h; Schlenk technique;90%
Stage #1: diphenylphosphane With α-Ln(α-deprotonated dimethylbenzylamine)3 In tetrahydrofuran Schlenk technique;
Stage #2: p-chlorphenylisocyanate In tetrahydrofuran at 20℃; for 6h; Schlenk technique;
83%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

phenethylamine
64-04-0

phenethylamine

3-(4-chlorophenyl)-1-(2-phenylethyl)urea

3-(4-chlorophenyl)-1-(2-phenylethyl)urea

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;99%
In dichloromethane for 2h; Reflux;72%
In chloroform at 60℃; for 16h;63%
C32H50O9
1571914-67-4

C32H50O9

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

C39H54ClNO10
1571914-90-3

C39H54ClNO10

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; Inert atmosphere;99%
4-amino-3,4-dihydro-2,2-dimethyl-6-ethylsulfonylamino-2H-1-benzopyran
1613108-50-1

4-amino-3,4-dihydro-2,2-dimethyl-6-ethylsulfonylamino-2H-1-benzopyran

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

N-4-chlorophenyl-N'-(6-ethylsulfonylamino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)urea
1613108-47-6

N-4-chlorophenyl-N'-(6-ethylsulfonylamino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)urea

Conditions
ConditionsYield
In dichloromethane for 0.5h; Reflux;99%
pyrrolidine
123-75-1

pyrrolidine

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

N-(4-chlorophenyl)-1-pyrrolidinecarboxamide
35640-09-6

N-(4-chlorophenyl)-1-pyrrolidinecarboxamide

Conditions
ConditionsYield
With [{Ph2P(Se)NCH2CH2NPPh2(Se)}Ti(NMe2)2] In toluene at 25℃; for 1h; Schlenk technique; Inert atmosphere; Glovebox;99%
With [κ2-{(Ph2P-(=Se))}2NCH2(C5H4N)ZnCl2] In toluene at 25℃; Schlenk technique; Inert atmosphere;93%
With 1,6-anhydro-3,4-dideoxy-β-D-glycero-hexopyranos-2-ulose at 0 - 20℃; for 1h;86%
at 20℃; for 2h; Molecular sieve; Inert atmosphere;
9-amino-9-deoxy-epi-cinchonidine

9-amino-9-deoxy-epi-cinchonidine

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

1-(4-chlorophenyl)-3-[(8α,9S)-cinchonan-9-yl]urea

1-(4-chlorophenyl)-3-[(8α,9S)-cinchonan-9-yl]urea

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃;99%
p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

N-propanoyl-1,3-thiazolidine-2-thione
85260-51-1

N-propanoyl-1,3-thiazolidine-2-thione

N-(4-chlorophenyl)-2-thioxothiazolidine-3carboxamide

N-(4-chlorophenyl)-2-thioxothiazolidine-3carboxamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃;99%
(1′S,2S,3S)-1-(1′-phenylethyl)-2-phenyl-3-aminoazetidine

(1′S,2S,3S)-1-(1′-phenylethyl)-2-phenyl-3-aminoazetidine

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

1-(4-chlorophenyl)-3-((2S,3S)-2-phenyl-1-((S)-1-phenylethyl)azetidin-3-yl)urea

1-(4-chlorophenyl)-3-((2S,3S)-2-phenyl-1-((S)-1-phenylethyl)azetidin-3-yl)urea

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5h;99%

104-12-1Relevant articles and documents

Chloride transport activities of trans- and cis-amide-linked bisureas

Park, Eun Bit,Jeong, Kyu-Sung

, p. 9197 - 9200 (2015)

Of the bisurea compounds linked through trans- and cis-benzanilide spacers, the cis-amide derivatives were found to be effective in chloride transport, using which a stimuli-responsive mobile carrier was devised. This journal is

Sulfonylureas as Concomitant Insulin Secretagogues and NLRP3 Inflammasome Inhibitors

Hill, James R.,Coll, Rebecca C.,Sue, Nancy,Reid, Janet C.,Dou, Jennifer,Holley, Caroline L.,Pelingon, Ruby,Dickinson, Joshua B.,Biden, Trevor J.,Schroder, Kate,Cooper, Matthew A.,Robertson, Avril A. B.

, p. 1449 - 1457 (2017)

Insulin-secretory sulfonylureas are widely used, cost-effective treatments for type 2 diabetes (T2D). However, pancreatic β-cells are continually depleted as T2D progresses, thereby rendering the sulfonylurea drug class ineffective in controlling glycaemia. Dysregulation of the innate immune system via activation of the NLRP3 inflammasome, and the consequent production of interleukin-1β, has been linked to pancreatic β-cell death and multiple inflammatory complications of T2D disease. One proposed strategy for treating T2D is the use of sulfonylurea insulin secretagogues that are also NLRP3 inhibitors. We report the synthesis and biological evaluation of nine sulfonylureas that inhibit NLRP3 activation in murine bone-marrow- derived macrophages in a potent, dose-dependent manner. Six of these compounds inhibited NLRP3 at nanomolar concentrations and can also stimulate insulin secretion from a murine pancreatic cell line (MIN6). These novel compounds possess unprecedented dual modes of action, paving the way for a new generation of sulfonylureas that may be useful as therapeutic candidates and/or tool compounds in T2D and its associated inflammatory complications.

Design, synthesis and structure-activity relationship study of novel urea compounds as FGFR1 inhibitors to treat metastatic triple-negative breast cancer

Akwii, Racheal,Alvina, Karina,Ashraf-Uz-Zaman, Md,Farshbaf, Mohammad Jodeiri,German, Nadezhda A.,Kallem, Raja Reddy,Mikelis, Constantinos M.,Putnam, William,Sajib, Md Sanaullah,Shahi, Sadisna,Trippier, Paul C.,Wang, Wei,Zhang, Ruiwen

, (2020/10/12)

Triple-negative breast cancer (TNBC) is an aggressive type of cancer characterized by higher metastatic and reoccurrence rates, where approximately one-third of TNBC patients suffer from the metastasis in the brain. At the same time, TNBC shows good responses to chemotherapy, a feature that fuels the search for novel compounds with therapeutic potential in this area. Recently, we have identified novel urea-based compounds with cytotoxicity against selected cell lines and with the ability to cross the blood-brain barrier in vivo. We have synthesized and analyzed a library of more than 40 compounds to elucidate the key features responsible for the observed activity. We have also identified FGFR1 as a molecular target that is affected by the presence of these compounds, confirming our data using in silico model. Overall, we envision that these compounds can be further developed for the potential treatment of metastatic breast cancer.

Supporting-Electrolyte-Free Anodic Oxidation of Oxamic Acids into Isocyanates: An Expedient Way to Access Ureas, Carbamates, and Thiocarbamates

Petti, Alessia,Fagnan, Corentin,van Melis, Carlo G. W.,Tanbouza, Nour,Garcia, Anthony D.,Mastrodonato, Andrea,Leech, Matthew C.,Goodall, Iain C. A.,Dobbs, Adrian P.,Ollevier, Thierry,Lam, Kevin

supporting information, p. 2614 - 2621 (2021/06/27)

We report a new electrochemical supporting-electrolyte-free method for synthesizing ureas, carbamates, and thiocarbamates via the oxidation of oxamic acids. This simple, practical, and phosgene-free route includes the generation of an isocyanate intermediate in situ via anodic decarboxylation of an oxamic acid in the presence of an organic base, followed by the one-pot addition of suitable nucleophiles to afford the corresponding ureas, carbamates, and thiocarbamates. This procedure is applicable to different amines, alcohols, and thiols. Furthermore, when single-pass continuous electrochemical flow conditions were used and this reaction was run in a carbon graphite Cgr/Cgr flow cell, urea compounds could be obtained in high yields within a residence time of 6 min, unlocking access to substrates that were inaccessible under batch conditions while being easily scalable.

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

Hong, Wan Pyo,Tran, Van Hieu,Kim, Hee-Kwon

, p. 15890 - 15895 (2021/05/19)

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.

Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus

Ruan, Banfeng,Zhang, Yuezhou,Tadesse, Solomon,Preston, Sarah,Taki, Aya C.,Jabbar, Abdul,Hofmann, Andreas,Jiao, Yaqing,Garcia-Bustos, Jose,Harjani, Jitendra,Le, Thuy Giang,Varghese, Swapna,Teguh, Silvia,Xie, Yiyue,Odiba, Jephthah,Hu, Min,Gasser, Robin B.,Baell, Jonathan

supporting information, (2020/02/04)

Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78–22.4 μM) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization.

Synthesis and biological evaluation of a new series of 1-aryl-3-[4-(pyridin-2-ylmethoxy)phenyl]urea derivatives as new anticancer agents

Feng, Jian,Li, Tai,Liang, Shishao,Zhang, Chuanming,Tan, Xiaoyu,Ding, Ning,Wang, Xin,Liu, Xiaoping,Hu, Chun

, p. 1413 - 1423 (2020/05/22)

The diaryl ureas are very important fragments in medicinal chemistry. By means of computer-aided design, 1-aryl-3-[4-(pyridin-2-ylmethoxy)phenyl]urea derivatives were designed and synthesized, and evaluated for their antiproliferative activity against A549, HCT-116, PC-3 cancer cell lines, and HL7702 human normal liver cell lines in vitro by using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide colorimetric assay. Most of the target compounds demonstrate significant antiproliferative effects on all the selective cancer cell lines. The calculated IC50 values were reported. The target compound 1-(4-chlorophenyl)-3-{4-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methoxy}phenyl}urea (7u) demonstrated the most potent inhibitory activity (IC50 = 2.39 ± 0.10 μM for A549 and IC50 = 3.90 ± 0.33 μM for HCT-116), comparable to the positive-control sorafenib (IC50 = 2.12 ± 0.18 μM for A549 and IC50 = 2.25 ± 0.71 μM for HCT-116). Conclusively, 1-aryl-3-[4-(pyridin-2-ylmethoxy)phenyl]urea derivatives as the new anticancer agents were discovered, and could be used as the potential BRAF inhibitors for further research.

Discovery of SP-96, the first non-ATP-competitive Aurora Kinase B inhibitor, for reduced myelosuppression

Lakkaniga, Naga Rajiv,Zhang, Lingtian,Belachew, Binyam,Gunaganti, Naresh,Frett, Brendan,Li, Hong-yu

, (2020/07/25)

Aurora Kinase B is a serine-threonine kinase known to be overexpressed in several cancers, with no inhibitors approved for clinical use. Herein, we present the discovery and optimization of a series of novel quinazoline-based Aurora Kinase B inhibitors. The lead inhibitor SP-96 shows sub-nanomolar potency in Aurora B enzymatic assays (IC50 = 0.316 ± 0.031 nM). We identified the important pharmacophore features resulting in selectivity against receptor tyrosine kinases. Particularly, SP-96 shows >2000 fold selectivity against FLT3 and KIT which is important for normal hematopoiesis. This could diminish the adverse effect of neutropenia reported in the clinical trials of the Aurora B inhibitor Barasertib, which inhibits FLT3 and KIT in addition to Aurora B. Enzyme kinetics of SP-96 shows non-ATP-competitive inhibition which makes it a first-in-class inhibitor. Further, SP-96 shows selective growth inhibition in NCI60 screening, including inhibition of MDA-MD-468, a Triple Negative Breast Cancer cell line.

Hit-to-lead optimization of novel benzimidazole phenylacetamides as broad spectrum trypanosomacides

Avery, Vicky M.,Baell, Jonathan,McNamara, Nicole,Rahmani, Raphael,Sykes, Melissa L.

supporting information, p. 685 - 695 (2020/08/24)

Trypanosoma cruzi and Trypanosoma brucei are the parasitic causative agents of Chagas disease and human African trypanosomiasis (HAT), respectively. The drugs currently used to treat these diseases are not efficacious against all stages and/or parasite sub-species, often displaying side effects. Herein, we report the SAR exploration of a novel hit, 2-(4-chlorophenyl)-N-(1-propyl-1H-benzimidazol-2-yl)acetamide previously identified from high throughput screens against T. cruzi, Trypanosoma brucei brucei and Leishmania donovani. An informative set of analogues was synthesized incorporating key modifications of the scaffold resulting in improved potency whilst the majority of compounds retained low cytotoxicity against H9c2 and HEK293 cell lines. The SAR observed against T. cruzi broadly matches that observed against T.b. brucei, suggesting the possibility for a broad-spectrum candidate. This class of compounds therefore warrants further investigation towards development as a treatment for Chagas disease and HAT. This journal is

Design, synthesis and antitumor assessment of phenylureas bearing 5-fluoroindolin-2-one moiety

Cai, Yunrui,Chen, Tong,Zhu, Huajian,Zou, Hongbin

, p. 958 - 968 (2020/08/19)

Background: The development of novel antineoplastic agents remains highly desirable. Objective: This study focuses on the design, synthesis, and antitumor evaluation of phenyl ureas bearing 5-fluoroindolin-2-one moiety. Methods: Three sets of phenylureas were designed and synthesized and their antiproliferative abil-ity was measured against four human carcinoma cell lines (Hela, Eca-109, A549, and MCF-7) via MTT assay. In vivo anticancer activity was further evaluated in xenograft models of human breast cancer (MCF-7). Results: A total of twenty-one new compounds were synthesized and characterized by means of1 H and13 C NMR as well as HR-MS. Three sets of compounds (1a?1c, 2a?2c, and 3a?3c) were ini-tially constructed, and preliminary antiproliferative activities of these molecules were evaluated against Hela, Eca-109, A549 and MCF-7, highlighting the meta-substituted phenylureas (1a?1c) as the most cytotoxic set. A series of meta-substituted phenylureas derivatives (1d?1o) were then designed and synthesized for structure-activity relationship study. Most of the new compounds showed desirable cytotoxicity, among which compound 1g exhibited the most remarkable cyto-toxic effects against the tested human cancer cells with IC50 values ranging from 1.47 to 6.79 μM. Further studies showed that compound 1g suppressed tumor growth in human breast cancer (MCF-7) xenograft models without affecting the body weight of its recipients. Conclusion: In this study, twenty-one new compounds, containing the privileged structures of phenylurea and 5-fluoroindolin-2-one, were designed and synthesized. Subsequent structure-activity studies showed that 1g was the most bioactive antitumor agent among all tested com-pounds, hence a potentially promising lead compound once given further optimization.

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