7693-46-1

Basic information

• Product Name: 4-Nitrophenyl chloroformate
• Synonyms: 4-Nitrophenyl chloridocarbonate;Formic acid, chloro-, p-nitrophenyl ester;p-Nitrophenoxycarbonyl chloride;CARBONOCHLORIDIC ACID, 4-NITROPHENYL ESTER;CHLOROFORMIC ACID 4-NITROPHENYL ESTER;CHLOROFORMIC ACID P-NITROPHENYL ESTER;4-NITROPHENYL CHLOROCARBONATE;4-NITROPHENYL CHLOROFORMATE
• CAS NO: 7693-46-1
• Molecular Formula: C₇H₄ClNO₄
• Molecular Weight: 201.56
• EINECS: 231-706-9
• Product Categories: blocks;BuildingBlocks;NitroCompounds;Miscellaneous;Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Pharmaceutical intermediates
• Mol File: 7693-46-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 77-79 °C(lit.)
• Boiling Point: 159-162 °C19 mm Hg(lit.)
• Flash Point: >110°C
• Appearance: White to yellow-beige/isopropanol suspension
• Density: 1.5719 (rough estimate)
• Vapor Pressure: 0.00312mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in acetone, chloroform, acetone, toluene and benzene.
• Water Solubility: decomposes
• Sensitive: Lachrymatory
• Stability: Stable. Incompatible with strong bases, acids. Combustible.
• BRN: 518127
• CAS DataBase Reference: 4-Nitrophenyl chloroformate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrophenyl chloroformate(7693-46-1)
• EPA Substance Registry System: 4-Nitrophenyl chloroformate(7693-46-1)

Safety Data

• Hazard Codes: C,T,Xi,F
• Statements: 34-36/37-23/24/25-41-36/37/38-11-67-36
• Safety Statements: 26-36/37/39-45-38-28A-36-16-27
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 7693-46-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 7693-46-1 differently. You can refer to the following data:
1. 4-Nitrophenyl Chloroformate is an ester of chloroformic acid used in the immobilization of enzymes and other biomolecules.
2. 4-Nitrophenyl chloroformate is used in the synthesis of poly(oxyethylene) modified dextrans. It is also used to prepare a cleavable, heterobifunctional cross-linker for reversible conjugation of amines to thiol-modified DNA. Further, it is used in the synthesis of mixed, activated carbonates, thiocarbonates and activated urethanes. In addition to this, it is used in the preparation of 4-nitrophenyl diazoacetate with diazomethane.
3. 4-Nitrophenyl chloroformate can be used:As a reagent for the activation of amines, alcohols and thiols.In the synthesis of 4-substituted phenyl derivatives of 1,2,4-triazolidindiones (urazoles).In the solid-phase synthesis of 3-aryl-2,4-quinazolinedione derivatives with potent anti-cancer property.In the preparation of poly(oxyethylene) modified dextrans.To synthesize a cleavable, heterobifunctional cross-linker for reversible conjugation of amines to thiol-modified DNA.

InChI:InChI=1/C7H4ClNO4/c8-7(10)13-6-3-1-5(2-4-6)9(11)12/h1-4H

Synthetic route

4-nitro-phenol (100-02-7) + bis(trichloromethyl) carbonate (32315-10-9) → 4-Nitrophenyl chloroformate (7693-46-1)

Conditions	Yield
With N,N-diethylaniline In toluene at 0℃; for 1h;	95%
With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 75℃; for 0.5h; Inert atmosphere;
With triethylamine In tetrahydrofuran at 0 - 20℃; for 6.25h; Inert atmosphere;

phosgene (75-44-5) + 4-nitro-phenol (100-02-7) → 4-Nitrophenyl chloroformate (7693-46-1)

Conditions	Yield
With potassium carbonate In dichloromethane at 25℃; Green chemistry;	92%
With N,N-dimethyl-aniline; triethylamine

4-nitro-phenol (100-02-7) + trichloromethyl chloroformate (503-38-8) → 4-Nitrophenyl chloroformate (7693-46-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane 1.) 0 deg C, 0.5 h, 2.) reflux, 2 h;	90%
With N-ethyl-N,N-diisopropylamine In dichloromethane Heating;	36%

phosgene (75-44-5) + 4-nitrophenol sodium salt (824-78-2) → 4-Nitrophenyl chloroformate (7693-46-1)

phosgene (75-44-5) + sodium salt of p-nitro-phenol → 4-Nitrophenyl chloroformate (7693-46-1)

Conditions	Yield
With benzene

3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (103421-61-0) + m-phenylenediamine (108-45-2) → N-{1,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl}-N'-{[3-(amino)phenyl]urea} + 4-Nitrophenyl chloroformate (7693-46-1)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide

4-nitro-phenol (100-02-7) → 4-Nitrophenyl chloroformate (7693-46-1)

Conditions	Yield
Stage #1: 4-nitro-phenol With bis(trichloromethyl) carbonate In dichloromethane at 0℃; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Heating / reflux;

dexamethasone (50-02-2) + 4-Nitrophenyl chloroformate (7693-46-1) → dexamethasone 21-(p-nitrophenyl carbonate) (79360-11-5)

Conditions	Yield
With pyridine In chloroform Ambient temperature;	100%
With pyridine In dichloromethane at 20℃; for 0.4h; Sealed tube;	72%
With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;	55%
With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 4h;
With pyridine at 20℃; for 2h; Concentration;

4-Nitrophenyl chloroformate (7693-46-1) + 5-O-(tert-butyldimethylsilyl)avermectin B1a (81924-41-6) → 5-O-(tert-butyldimethylsilyl)-4''-O-<<(4-nitrophenyl)oxy>carbonyl>avermectin B1a (81924-49-4)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h;	100%

4-Nitrophenyl chloroformate (7693-46-1) + 3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (69304-38-7) → 2′-O-(4-nitrophenoxycarbonyl)-3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (202533-73-1)

Conditions	Yield
With pyridine; dmap at 20℃; for 16h;	100%
In pyridine; toluene for 1h; Ambient temperature;	96%
With pyridine In toluene at 20℃; for 5h; Inert atmosphere;	81%

morpholine (110-91-8) + 4-Nitrophenyl chloroformate (7693-46-1) → morpholine-4-carboxylic acid 4-nitrophenyl ester (17376-42-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3.5h;	100%
With triethylamine In dichloromethane at 20℃; for 3.5h;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 3h; Acylation;	58%

tert-butyl (1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (122745-41-9, 130008-89-8, 130007-86-2) + 4-Nitrophenyl chloroformate (7693-46-1) → (S)-tert-butyl 1-(chloromethyl)-5-((4-nitrophenoxy)carbonyloxy)-1H-benzo[e]indole-3(2H)-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃;	100%
With triethylamine In dichloromethane at 25℃; for 2h; Substitution;
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 5h;

4-Nitrophenyl chloroformate (7693-46-1) + (2-Phenyl-2-trimethylsilyl)ethanol (122760-31-0) → (2-Phenyl-2-trimethylsilyl)ethyl 4-nitrophenyl carbonate (327026-58-4)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 4h;	100%

taxol (33069-62-4) + 4-azidobenzyl alcohol (31499-54-4) + 4-Nitrophenyl chloroformate (7693-46-1) → 2'-(4-azidobenzyloxycarbonyl)paclitaxel

Conditions	Yield
Stage #1: 4-azidobenzyl alcohol; 4-Nitrophenyl chloroformate With pyridine; dmap In dichloromethane for 0.666667h; Stage #2: taxol With dmap In dichloromethane for 70h;	100%

4-Nitrophenyl chloroformate (7693-46-1) + Nα-(9-fluorenylmethoxycarbonyl)-D-serine-tert-butyl ether (71989-33-8, 128107-47-1) → 3-tert-butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 4-nitro-phenyl ester (439905-03-0)

Conditions	Yield
Stage #1: 4-Nitrophenyl chloroformate; Nα-(9-fluorenylmethoxycarbonyl)-D-serine-tert-butyl ether With TEA In dichloromethane at 0℃; for 0.25h; Stage #2: With dmap at 0℃; for 0.5h;	100%

4-Nitrophenyl chloroformate (7693-46-1) + benzylamine (100-46-9) + (6-hydroxymethyl-naphthalen-2-yl)-carbamic acid allyl ester (393521-87-4) → (6-benzylcarbamoyloxymethyl-naphthalen-2-yl)-carbamic acid allyl ester (393521-89-6)

Conditions	Yield
Stage #1: 4-Nitrophenyl chloroformate; (6-hydroxymethyl-naphthalen-2-yl)-carbamic acid allyl ester In tetrahydrofuran; pyridine at 20℃; for 4h; Stage #2: benzylamine In tetrahydrofuran; pyridine at 20℃; for 19h; Further stages.;	100%

4-Nitrophenyl chloroformate (7693-46-1) + benzylamine (100-46-9) + (4'-hydroxymethyl-biphenyl-4-yl)-carbamic acid allyl ester (393522-89-9) → (4'-benzylcarbamoyloxymethyl-biphenyl-4-yl)-carbamic acid allyl ester (393522-92-4)

Conditions	Yield
Stage #1: 4-Nitrophenyl chloroformate; (4'-hydroxymethyl-biphenyl-4-yl)-carbamic acid allyl ester With triethylamine In tetrahydrofuran at 20℃; for 19h; Stage #2: benzylamine In tetrahydrofuran for 21h; Further stages.;	100%

4-Nitrophenyl chloroformate (7693-46-1) + C49H57N7O12 (393522-16-2) → Carbonic acid 4-[4-(4-{(S)-6-allyloxycarbonylamino-2-[(S)-2-((R)-2-allyloxycarbonylamino-propionylamino)-3-phenyl-propionylamino]-hexanoylamino}-benzyloxycarbonylamino)-benzyloxycarbonylamino]-benzyl ester 4-nitro-phenyl ester (393522-19-5)

Conditions	Yield
In tetrahydrofuran; pyridine; dichloromethane at -40 - 6℃; for 48h;	100%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-Nitrophenyl chloroformate (7693-46-1) → N-(4-nitrophenoxycarbonyloxy)succinimide (371783-15-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 0.5h;	100%

4-(diisopropylsilanyl)-phenyl methanol (475160-70-4) + 4-Nitrophenyl chloroformate (7693-46-1) → carbonic acid 4-(diisopropyl-silanyl)-benzyl ester 4-nitrophenyl ester

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane for 0.75h;	100%

4-methoxy-aniline (104-94-9) + 4-Nitrophenyl chloroformate (7693-46-1) → 4-nitrophenyl (4-methoxyphenyl)carbamate (4058-71-3)

Conditions	Yield
With pyridine In dichloromethane for 72h;	100%
With pyridine In dichloromethane at 20℃;
With sodium hydrogencarbonate In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;
With pyridine In tetrahydrofuran at 0℃; Inert atmosphere;

4-methyl-benzaldehyde (104-87-0) + 4-Nitrophenyl chloroformate (7693-46-1) → O-(4-nitrophenyl)-N-(4-tolyl)carbamate (3848-42-8)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 0.5h;	100%

4-Nitrophenyl chloroformate (7693-46-1) + 4-(2-keto-1-benzimidazolinyl)piperidine (20662-53-7) → C19H18N4O5 (633312-78-4)

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane	100%
With triethylamine In 1,2-dichloro-ethane for 1h; Heating / reflux;	100%

(8E,12E,14E)-7-acetoxy-6,21-dihydroxy-6,10,12,16,20-pentamethyl-3-(4-nitrophenoxycarboxy)-18,19-epoxytricosa-8,12,14-trien-11-olide + 4-Nitrophenyl chloroformate (7693-46-1) → (8E,12E,14E)-7-acetoxy-3-carbamoyloxy-6,21-dihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide

Conditions	Yield
With ammonia In tetrahydrofuran; water for 21.5h;	100%

L-tert-leucine methyl ester hydrochloride (63038-27-7) + 4-Nitrophenyl chloroformate (7693-46-1) → methyl (2S)-3,3-dimethyl-2-{[(4-nitrophenoxy)carbonyl]amino}butanoate (854755-78-5)

Conditions	Yield
With 4-methyl-morpholine In dichloromethane at 25℃; for 64h;	100%

methyl 2(S)-ethoxy-3-[6-(3-methylaminophenyl)pyrid-3-yl]propanoate (817618-70-5) + 4-Nitrophenyl chloroformate (7693-46-1) → methyl 2(S)-ethoxy-3-(6-{3-[methyl(4-nitrophenoxycarbonyl)amino]phenyl}pyrid-3-yl)propanoate (817618-71-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	100%

methyl 2(S)-ethoxy-3-[4-(6-methylaminopyrid-2-yl)phenyl]propanoate (817618-76-1) + 4-Nitrophenyl chloroformate (7693-46-1) → methyl 2(S)-ethoxy-3-(4-{6-[methyl(4-nitrophenoxycarbonyl)amino]pyrid-2-yl}phenyl)propanoate (817618-75-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1.5h;	100%

(R)-methyl 2-hydroxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)propanoate (855778-06-2) + 4-Nitrophenyl chloroformate (7693-46-1) → (R)-methyl 3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)-2-((4-nitrophenoxy)carbonyloxy)propanoate (855778-07-3)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;	100%
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;	100%

methyl 3-(2-((2-(trimethylsilyl)ethoxy)methyl)-7-methyl-2H-indazol-5-yl)-2-hydroxypropanoate (855778-80-2) + 4-Nitrophenyl chloroformate (7693-46-1) → 1-(methoxycarbonyl)-2-(2-((2-(trimethylsilyl)ethoxy)methyl)-7-methyl-2H-indazol-5-yl)ethyl 4-nitrophenyl carbonate (855778-81-3)

Conditions	Yield
With pyridine at 20℃;	100%
With pyridine at 20℃;	100%

(8E,12E,14E)-7-hydroxy-6,10,12,16,20-pentamethyl-3,16,21-tris(triethylsiloxy)-18,19-epoxytricosa-8,12,14-trien-11-olide + 4-Nitrophenyl chloroformate (7693-46-1) → (8E,12E,14E)-6,10,12,16,20-pentamethyl-7-((4-nitrophenoxy)carboxy)-3,16,21-tris(triethylsiloxy)-18,19-epoxytricosa-8,12,14-trien-11-olide

Conditions	Yield
With dmap; triethylamine In dichloromethane at 5℃; for 1h;	100%

(R)-2-hydroxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-1-one (865626-75-1) + 4-Nitrophenyl chloroformate (7693-46-1) → (R)-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-nitrophenyl carbonate (865626-76-2)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	100%
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane

tert-butyl 4-{[4-(aminomethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate (871021-84-0) + 4-Nitrophenyl chloroformate (7693-46-1) → tert-butyl 4-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate (871021-85-1)

Conditions	Yield
Stage #1: 4-Nitrophenyl chloroformate; 1,3-dihydro-1-(1-methylethyl)-2H-benzimidazol-2-one With triethylamine In dichloromethane at 20℃; for 4h; Stage #2: tert-butyl 4-{[4-(aminomethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate In dichloromethane at 20℃; for 24h;	100%

4-methyl-3-(1-{[4-(2,4,5-trifluorophenoxy)phenyl]methyl}(4-piperidyl))phenylamine (882745-59-7) + 4-Nitrophenyl chloroformate (7693-46-1) → N-[4-methyl-3-(1-{[4-(2,4,5-trifluorophenoxy)phenyl]methyl}(4-piperidyl))phenyl](4-nitrophenoxy)carboxamide (882746-18-1)

Conditions	Yield
With pyridine In dichloromethane for 5h; Heating / reflux;	100%
With pyridine In dichloromethane for 5h; Heating / reflux;	100%

C17H16FN3OS*ClH + 4-Nitrophenyl chloroformate (7693-46-1) → C24H19FN4O5S

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1h;	100%

N-(2-aminoethyl)-2,3-dichloro-N-methylbenzenesulphonamide trifluoroacetate (1114225-30-7) + 4-Nitrophenyl chloroformate (7693-46-1) → 4-nitrophenyl {2-[(2,3-dichlorobenzenesulphonyl)methylamino]ethyl}carbamate (886236-65-3)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 1h;	100%

(3R*,4R*)-N-[3,5-bis(trifluoromethyl)benzyl]-N-methyl-3-phenylpiperidine-4-carboxamide hydrochloride + 4-Nitrophenyl chloroformate (7693-46-1) → C29H25F6N3O5*ClH

Conditions	Yield
Stage #1: (3R*,4R*)-N-[3,5-bis(trifluoromethyl)benzyl]-N-methyl-3-phenylpiperidine-4-carboxamide hydrochloride; 4-Nitrophenyl chloroformate With triethylamine In dichloromethane at 20℃; for 1h; Stage #2: With ammonium chloride In dichloromethane; water; ethyl acetate	100%

3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenol (885066-89-7) + 4-Nitrophenyl chloroformate (7693-46-1) → carbonic acid 3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl ester 4-nitro-phenyl ester (885068-19-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	100%

Upstream product

• 100-02-7 4-nitro-phenol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 103421-61-0 3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one 
• 108-45-2 m-phenylenediamine 
• 75-44-5 phosgene 
• 503-38-8 trichloromethyl chloroformate 
• 824-78-2 4-nitrophenol sodium salt 

Downstream Products

• 77637-89-9 p-nitrophenyl 2-pyridylpropyl carbonate 
• 135484-55-8 4-nitrophenyl 1H-pyrrole-1-carboxylate 
• 3401-37-4 S-benzyl-N-carbobenzoxy-L-cysteine p-nitrophenyl ester 
• 73717-05-2 p-Nitrophenyl-o-chlorbenzylcarbonat 
• 10512-93-3 Z-Val-ONp 
• 7763-16-8 N²-benzyloxycarbonyl-L-glutamine-(4-nitro-phenyl ester) 
• 2419-54-7 N-(benzyloxycarbonyl)-β-benzyl-L-aspartic acid p-nitrophenyl ester 
• 3562-03-6 Z-Tyr(OBzl)-ONp 
• 17374-48-0 Salicylsaeure-4-nitrophenylester 
• 13795-24-9 benzyl 4-nitrophenyl carbonate 
• 6453-62-9 4-nitrophenyl 3,5-dimethoxybenzyl carbonate 
• 31558-54-0 3,4-dimethoxybenzyl 4-nitrophenyl carbonate 
• 13303-10-1 tert-Butyl 4-nitrophenyl carbonate 
• 101874-85-5 carbonic acid-(5-acetyl-[8]quinolyl ester)-(4-nitro-phenyl ester) 

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