6780-38-7

Usage

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 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 108-42-9 3-chloro-aniline 
• 4743-52-6 N-(o-carboxybenzoyl)glycine 
• 85-44-9 phthalic anhydride 
• 22509-74-6 N-ethoxycarbonylphthalimide 

Downstream Products

• 6343-09-5 1-(N,N-phthaloyl-glycyl)-aziridine 
• 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 
• 3321-03-7 Gly-Phe-OH 
• 1170-07-6 N-(N,N-phthaloyl-glycyl)-L-phenylalanine 

Relevant academic research and scientific papers

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.

Amino acid conjugates of aminothiazole and aminopyridine as potential anticancer agents: Synthesis, molecular docking and in vitro evaluation

Purpose: The development of resistance to available anticancer drugs is increasingly becoming a major challenge and new chemical entities could be unveiled to compensate this therapeutic failure. The current study demonstrated the synthesis of 2-aminothiazole [S3 (a-d) and S5(a-d)] and 2-aminopyridine [S4(a-d) and S6(a-d)] derivatives that can target multiple cellular networks implicated in cancer development. Methods: Biological assays were performed to investigate the antioxidant and anticancer potential of synthesized compounds. Redox imbalance and oxidative stress are hallmarks of cancer, therefore, synthesized compounds were preliminarily screened for their antioxidant activity using DPPH assay, and further five derivatives S3b, S3c, S4c, S5b, and S6c, with significant antioxidant potential, were selected for investigation of in vitro anticancer potential. The cytotoxic activities were evaluated against the parent (A2780) and cisplatin-resistant (A2780CISR) ovarian cancer cell lines. Further, Molecular docking studies of active compounds were performed to determine binding affinities. Results: Results revealed that S3c, S5b, and S6c displayed promising inhibition in cisplatin-resistant cell lines in comparison to parent cells in terms of both resistance factor (RF) and IC50 values. Moreover, S3c proved to be most active compound in both parent and resistant cell lines with IC50 values 15.57 μM and 11.52 μM respectively. Our docking studies demonstrated that compounds S3c, S5b, and S6c exhibited significant binding affinity with multiple protein targets of the signaling cascade. Conclusion: Anticancer activities of compounds S3c, S5b, and S6c in cisplatin-resistant cell lines suggested that these ligands may contribute as lead compounds for the development of new anticancer drugs.

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.

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

The present invention relates to compound-linker constructs and antibody-drug-conjugates of compounds of formula (I) that are useful as modulators of STING (Stimulator of Interferon Genes).

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.

THERAPEUTIC COMPOUNDS

The present invention relates to compounds that are Nrf2 activators. The compounds have the structural formula I defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of diseases or disorders associated with Nrf2 activation.

Synthesis of New Methanofullerenes with Phthalimide Fragment

Abstract: Bromo- and chloromethyl ketones based on N-phthalyl-substituted amino acids have been synthesized via the Arndt–Eistert reaction. The products [2+1] cycloaddition to the fullerene scaffold has afforded the monoadducts of fullerene C60.

A Convenient One-Pot Synthesis of 1,5-Disubstituted Tetrazoles Containing an Amino or a Carboxy Group

Abstract: A convenient method is proposed for constructing the tetrazole ring by a one-pot reaction of amides with phosphorus oxychloride and sodium azide. A series of 1,5-disubstituted tetrazoles containing an amino or a carboxy group, which present interest as buildings blocks for the synthesis of biologically active substances, were obtained.

A CONJUGATE OF AN AMANITA TOXIN WITH BRANCHED LINKERS

Provided herein is the conjugation of an amanita toxin compound to a cell-binding molecule with branched linkers for having better targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of an amanita molecule to a cell-binding ligand, as well as methods of using the conjugate in targets treatment of cancer, infection and autoimmune disease.

AMINO ACID DERIVATIVES FOR THE TREATMENT OF INFLAMMATORY DISEASES

The present disclosure provides certain amino acid derivatives that inhibit NF-kB activation and are therefore useful for the treatment of inflammatory diseases. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.