6780-38-7

Basic information

• Product Name: Phthalylglycyl chloride
• Synonyms: 1,3-dihydro-1,3-dioxo-2h-isoindole-2-acetylchlorid;PHTHALYL-GLYCYL CHLORIDE;1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetyl chloride;N-Phthalylglycyl chloride;N-Phthalylglycyl chloride(Phthalimide acetyl chloride);(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl chloride;Phthalyl-glycyl chloride ,98%;(1,3-Dioxo-2H-isoindole-2-yl)acetyl chloride
• CAS NO: 6780-38-7
• Molecular Formula: C₁₀H₆ClNO₃
• Molecular Weight: 223.61
• EINECS: 229-840-8
• Product Categories: pharmacetical;Acid Halides;Carbonyl Compounds;Organic Building Blocks;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Heterocycle-other series
• Mol File: 6780-38-7.mol
• Article Data: 87

Chemical Properties

• Melting Point: 84-85 °C
• Boiling Point: 343.2 °C at 760 mmHg
• Flash Point: 161.4 °C
• Appearance: slight yellow to white crystalline powder
• Density: 1.504 g/cm³
• Vapor Pressure: 7.14E-05mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform, Dichloromethane
• PKA: -2.56±0.20(Predicted)
• CAS DataBase Reference: Phthalylglycyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Phthalylglycyl chloride(6780-38-7)
• EPA Substance Registry System: Phthalylglycyl chloride(6780-38-7)

Safety Data

• Hazard Codes: T
• Statements: 25-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2923 8/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 6780-38-7(Hazardous Substances Data)

Usage

Description

Phthalylglycyl chloride is an organic compound synthesized through the reaction of phthalyl-glycine with thionyl chloride. It is a key intermediate in the synthesis of various pharmaceuticals and organic compounds.

Uses

Used in Pharmaceutical Industry:
Phthalylglycyl chloride is used as a reactant for the synthesis of selenium-containing amino acid analogs with bactericidal and antifungal activity. These analogs have potential applications in the development of new antimicrobial agents.
Used in Peptide Synthesis:
Phthalylglycyl chloride is used as a reactant in photoinduced single electron transfer cyclization for the preparation of cyclic peptides. This method allows for the efficient synthesis of cyclic peptides with potential applications in drug discovery and development.
Used in Organic Chemistry:
Phthalylglycyl chloride is used as a reactant in the Arndt-Eistert synthesis, a method for the preparation of α,β-unsaturated esters. This synthesis is useful for the preparation of various organic compounds with potential applications in pharmaceuticals, agrochemicals, and materials science.
Used in Multicomponent Reactions:
Phthalylglycyl chloride is used as a reactant in Mitsunobu and arbuzov-type multicomponent pathways. These reactions allow for the efficient synthesis of complex organic molecules with potential applications in various fields.
Used in C-H Bond Functionalization:
Phthalylglycyl chloride is used as a reactant in remote C-H bond functionalization, a method for the selective modification of specific C-H bonds in organic molecules. This technique is useful for the synthesis of complex organic compounds with potential applications in pharmaceuticals and materials science.
Used in Benzofuran Derivatives Synthesis:
Phthalylglycyl chloride is used as a reactant in amido-alkylation for the synthesis of benzofuran derivatives. These derivatives have potential applications in the development of new pharmaceuticals and agrochemicals.
General Description:
Phthalylglycyl chloride is a versatile intermediate in the synthesis of various organic compounds and pharmaceuticals. Its ability to participate in a wide range of reactions makes it a valuable building block in the development of new drugs and materials.

InChI:InChI=1/C10H6ClNO3/c11-8(13)5-12-9(14)6-3-1-2-4-7(6)10(12)15/h1-4H,5H2

Upstream product

• 4702-13-0 N-phthaloylglycine 
• 10026-13-8 phosphorus pentachloride 
• 85-44-9 phthalic anhydride 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 108-42-9 3-chloro-aniline 
• 4743-52-6 N-(o-carboxybenzoyl)glycine 

Downstream Products

• 6343-09-5 1-(N,N-phthaloyl-glycyl)-aziridine 
• 5442-90-0 2-[2-(morpholin-4-yl)-2-oxoethyl]isoindoline-1,3-dione 
• 860711-08-6 N-(7-oxo-5-phenyl-4-thia-1-aza-bicyclo[3.2.0]hept-6-yl)-phthalimide 
• 130987-61-0 N,N-phthaloyl-glycine-(2,4-dinitro-phenyl ester) 
• 21313-49-5 N,N-phthaloyl-glycine-(4-nitro-phenyl ester) 
• 861018-39-5 N-(4-phenoxy-phenacyl)-phthalimide 
• 111114-09-1 (3,4-Dimethoxyphenyl)-(phthalimidomethyl)-keton 
• 1154-45-6 N-phthaloyl-glycyl-α-alanine 
• 91841-16-6 N-(N,N-phthaloyl-glycyl)-DL-serine 
• 6707-71-7 N-(N,N-phthaloyl-glycyl)-L-leucine 
• 35181-18-1 N²-(N,N-phthaloyl-glycyl)-DL-asparagine 
• 1165-77-1 N-(N,N-phthaloyl-glycyl)-L-glutamic acid 
• 93923-88-7 N-[N-(N,N-phthaloyl-glycyl)-glycyl]-glycine 
• 5472-64-0 3-[4-(N,N-phthaloyl-glycyl)-phenyl]-propionic acid methyl ester 

Relevant articles and documents

Potent antiproliferative activity of bradykinin B2 receptor selective agonist FR-190997 and analogue structures thereof: A paradox resolved?

Βradykinin stimulation of B2 receptor is known to activate the oncogenic ERK pathway and overexpression of bradykinin receptors B1 and B2 has been reported to occur in glioma, colorectal and cervical cancers. B1R and B2R antagonists have been shown to reverse tumor proliferation and invasion. Paradoxically, B1R and B2R agonism has also been reported to elicit antiproliferative benefits. In order to complement the data accumulated to date with the natural substrate bradykinin and peptidic B2R antagonists, we decided to examine for the first time the response elicited by B2R stimulation in breast cancer lines with a non-peptidic small molecule B2R agonist. We synthesized and assessed the highly selective and potent B2R partial agonist FR-190997 in MCF-7 and MDA-MBA-231 breast cancer lines and found it possessed significant antiproliferative activity (IC50 2.14 and 0.08 μΜ, respectively). The modular nature of FR-190997 allowed us to conduct a focused SAR study and discover compound 10 which exhibits subnanomolar antiproliferative activity (IC 50 0.06 nΜ) in the TNBC MDA-MBA-231 cell line. This performance surpasses, in most cases by several orders of magnitude, those of established anticancer agents and FDA-approved breast cancer drugs. In line with the established literature we suggest that this remarkable activity precipitates from a dual mode of action involving agonist-induced receptor internalization/degradation combined with sequestration of functional intracellular B2 receptors and inhibition of the associated endosomal signaling. The latter mode may be realized by appropriate ligands regardless of B2R agonist/antagonist designation which only relates to membrane residing GCPRs. Under this prism the controversy over the antiproliferative effects of B2 agonists and antagonists is potentially neutralized.

HETEROCYCLIC COMPOUNDS AS MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)

The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.

Synthesis and Penicillin-binding Protein Inhibitory Assessment of Dipeptidic 4-Phenyl-β-lactams from α-Amino Acid-derived Imines

Monocyclic β-lactams revive the research field on antibiotics, which are threatened by the emergence of resistant bacteria. A six-step synthetic route was developed, providing easy access to new 3-amino-1-carboxymethyl-4-phenyl-β-lactams, of which the penicillin-binding protein (PBP) inhibitory potency was demonstrated biochemically.