52218-17-4

Basic information

• Product Name: 2-imino-2H-chromene-3-carboxamide
• Synonyms: 2-imino-2H-chromene-3-carboxamide;2-Iminochromene-3-carboxamide
• CAS NO: 52218-17-4
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.18272
• Mol File: 52218-17-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-imino-2H-chromene-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-imino-2H-chromene-3-carboxamide(52218-17-4)
• EPA Substance Registry System: 2-imino-2H-chromene-3-carboxamide(52218-17-4)

Safety Data

• Hazardous Substances Data: 52218-17-4(Hazardous Substances Data)

Upstream product

• 89-95-2 2-methyl-benzyl alcohol 
• 107-91-5 cyanoacetic acid amide 
• 90-02-8 salicylaldehyde 

Downstream Products

• 75586-44-6 2-p-Tolyl-2,3-dihydro-9-oxa-1,3-diaza-anthracen-4-one 
• 75586-49-1 2-p-Tolyl-10H-9-oxa-1,3-diaza-anthracen-4-ol 
• 129110-78-7 5-Imino-2-phenyl-3,5-dihydro-chromeno[3,4-c]pyridin-4-one 
• 79250-07-0 5-Imino-2-methyl-3,5-dihydro-chromeno[3,4-c]pyridin-4-one 
• 79250-14-9 2-Methyl-3H-chromeno[3,4-c]pyridine-4,5-dione 
• 79250-19-4 4-(2-Hydroxy-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile 
• 180403-60-5 2-(Benzoyl-hydrazono)-2H-chromene-3-carboxylic acid amide 
• 180403-52-5 N²-benzoyl-2-oxo-2H-chromene-3-carbohydrazonmide 
• 3695-88-3 2-hydroxy-α-cyanocinnamamide 
• 73877-78-8 2-oxo-2H-1-benzopyran-3-(N-2-carboxyphenyl)-carboxamide 
• 212207-07-3 2-[(N-2-carboxyphenyl)imino]coumarin-3-carboxamide 
• 313243-16-2 3-[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-one 
• 1272665-83-4 2-amino-3-cyano-N-cyclohexyl-4H-chromene-4-carboxamide 
• 75586-39-9 2-cyclohexyl-4-oxo-2,3-dihydrobenzopyrano<2,3-d>pyrimidine 

Relevant articles and documents

Discovery of 4H-chromeno[2,3-d]pyrimidin-4-one derivatives as senescence inducers and their senescence-associated antiproliferative activities on cancer cells using advanced phenotypic assay

Current research suggests therapy-induced senescence (TIS) of cancer cells characterized by distinct morphological and biochemical phenotypic changes represent a novel functional target that may enhance the effectiveness of cancer therapy. In order to identify novel small-molecule inducers of cellular senescence and determine the potential to be used for the treatment of melanoma, a new method of high-throughput screening (HTS) and high-contents screening (HCS) based on the detection of morphological changes was designed. This image-based and whole cell-based technology was applied to screen and select a novel class of antiproliferative agents on cancer cells, 4H-chromeno[2,3-d]pyrimidin-4-one derivatives, which induced senescence-like phenotypic changes in human melanoma A375 cells without serious cytotoxicity against normal cells. To evaluate structure-activity relationship (SAR) study of 4H-chromeno[2,3-d]pyrimidin-4-one scaffold starting from hit 3, a focused library containing diversely modified analogues was constructed and which led to the identification of 38, a novel compound to have remarkable anti-melanoma activity in vitro with good metabolic stability.

Reaction of 2-imino-2H-chromene-3-carboxamide with some phosphorus esters: Synthesis of some novel chromenes containing phosphorus heterocycles and phosphonate groups and their antioxidant and cytotoxicity properties

Novel chromenyl α-aminophosphonic acid 4 and dialkyl chromenyl phosphonate 6 have been obtained. In addition, some novel types of chromene fused with phosphorus heterocycles such as chromeno[4,3-c][1,2]azaphospholes 5 and 7, chromeno[2,3-d][1,3,2]diazaphosphinine 8 and 1,2-oxaphosphinino[3,4-c]pyridine 10 have been synthesized. The methodology depended on treatment of 2-imino-2H-chromene-3-carboxamide (1) with some phosphorus esters. The synthesized compounds were evaluated for antioxidant and cytotoxic activities. Among the synthesized compounds, compound 5 exhibited the most antioxidant activity with IC50 = 2.8 μg/mL in comparison with ascorbic acid as standard antioxidant. Also, compound 5 had significant cytotoxic effects against four cancer cell lines. Its IC50 values ranged between 4.96 and 7.44 μg/mL in comparison to doxorubicin (IC50 = 0.426–0.493 μg/mL).

Reaction of 2-Imino-2H-chromene-3-carboxamide with Phosphorus Isothiocyanates: First Synthesis of Novel Chromeno[2,3-d]pyrimidinyl and Bis(chromeno[2,3-d]pyrimidinyl)phosphines and Chromeno[2′,3′:4,5]pyrimido[2,1-d][1,3,5,2]triazaphosphinine

Novel chromeno[2,3-d]pyrimidinyl and bis(chromeno[2,3-d]pyrimidinyl)phosphines and chromeno[2′,3′:4,5]pyrimido[2,1-d][1,3,5,2]triazaphosphinine were obtained in a simple one-pot procedure via treatment of 2-imino-2H-chromene-3-carboxamide with phenyl phosphorus isothiocyanates. Possible reaction mechanisms were proposed. The structures of the obtained products were confirmed by elemental analyses and spectral tools.

Reaction of 2-imino-2H-chromene-3-carboxamide with phosphorus halides: Synthesis of some novel chromeno-[2,3-d][1,3,2]diazaphosphinines and chromeno[4,3-c][1,2]-azaphosphole and their antioxidant and cytotoxicity properties

Novel 1,2-azaphosphole and 1,3,2-diazaphosphinines containing a chromene ring have been obtained from the treatment of 2-imino-2H-chromene-3-carboxamide (1) with some phosphorus halides. The compounds were evaluated for antioxidant and cytotoxic activitie

Reaction of 2-imino-2H-chromene-3-carboxamide with phosphorus sulfides: Synthesis of novel 2-sulfido-2,3-dihydro-4H-chromeno[2,3-d][1,3,2]diaza-phosphinines

Novel 2-sulfido-2,3-dihydro-4H-chromeno[2,3-d][1,3,2]diazaphosphinines are obtained in a simple one-pot procedure via treatment of 2-imino-2H-chromene-3-carboxamide with various phosphorus sulfides. Possible reaction mechanisms are proposed. The structure

Synthesis of 2-amino-3-cyano-4H-chromene-4-carboxamide derivatives by an isocyanide-based domino conjugate addition/O-trapping rearrangement sequence

An efficient, one-pot domino synthesis of new 2-amino-3-cyano-4H-chromene- 4-carboxamide derivatives has been developed by the acid-induced conjugate addition of isocyanides to 2-imino-2H-chromene-3-carboxamides, followed by an intramolecular O-trapping r

New HA 14-1 analogues: Synthesis of 2-amino-4-cyano-4H-chromenes

The synthesis of 2-amino-4-cyano-4H-chromene derivatives as new HA 14-1 analogues by a simple and efficient method is reported. In addition, the reaction of 2-amino-2H-chromene-3-carbonitriles, salicylaldehydes and amines results in the formation of new c

Polymer supported reagents: Novel methodology for selective and general synthesis of iminocoumarins

A selective synthesis of iminocoumarins 3 was accomplished, starting from salicylaldehydes 1 and nitriles 2, by the use of Amberlite IRA 900 resin as a polymeric solid support. The possibility of using various arylacetonitriles enhances the synthetic vers

Structure and Reactivity of 2-Amino-3-carbamoylchromenylium Salts

A series of 3-substituted 2-aminochromenylium salts were synthesized, and their acid dissociation constants in 50 percent ethanol were measured at 20 deg C. 2-Amino-3-carbamoylchromenylium salts showed a correlation between log Ka values and Brown-Okamoto substituent coefficient constants ?+ (ρ = 0.99, r = 0.973). The constant ?+ for the quinolizine group was estimated at -2.9. A scale of acidity (H+) was proposed for solutions of HCl in 50 vol percent ethanol at 20 deg C (cHCl ,1.5 M). The effect of substituents in positions 3, 6, and 7 and methylation of the 2-amino group on the reactivity of 2-aminochromenylium salts is discussed.

Recyclization of 2-imino-2H-1-benzopyrans using nucleophilic reagents 3. Reaction of 2-iminocoumarin-3-carboxamides with o-phenylenediamines and o-amino(thio)phenols

Using o-phenylenediamines, o-aminophenol or o-aminothiophenol, 2-iminocoumarin-3-carboxamide can be recyclized to the corresponding 3-(1H-benzimidazol-2-yl), 3-(benzoxazol-2-yl), or 3-(benzothiazol-2-yl) coumarins. An alternative synthesis has been carried out and an analytical comparison of the synthetic routes made.