41808-11-1

Upstream product

• 3027-05-2 N,N'-diacetylpiperazin-2,5-dione 
• 100-52-7 benzaldehyde 
• 106-95-6 allyl bromide 
• 108-24-7 acetic anhydride 
• 19459-03-1 (Z)-3-phenylmethylenepiperazine-2,5-dione 

Downstream Products

• 74720-33-5 (Z)-3-(Z)-6-dibenzylidene-2,5-piperazinedione 
• 1222-90-8 (3Z,6Z)-3-benzylidene-6-(2-methylpropenyl)piperazine-2,5-dione 
• 117531-68-7 3-[2-Oxo-1,2-dihydro-indol-(3Z)-ylidene]-6-[1-phenyl-meth-(E)-ylidene]-piperazine-2,5-dione 
• 74720-35-7 (3Z,6Z)-6-Benzylidene-3-(4-methoxybenzylidene)-2,5-piperazinedione 
• 24719-39-9 3-benzylidene-2,5-piperazinedione 
• 1492924-32-9 1-acetyl-4-allyl-3-benzylidenepiperazine-2,5-dione 
• 5801-57-0 (Z)-2-hydroxy-3-phenyl-acrylic acid 
• 59552-69-1 (+/-)-1,4-diacetyl-3-benzylpiperazine-2,5-dione 
• 1235977-29-3 (+/-)-1-acetyl-6-benzylpiperazine-2,5-dione 
• 709615-07-6 (+/-)-1-acetyl-3-benzylpiperazine-2,5-dione 
• 1235977-27-1 (+/-)-t-butyl-3-[(Z)-(5-benzyl-3,6-dioxopiperazin-2-ylidene)methyl]-4-nitroindole-1-carboxylate 
• 1235977-25-9 (+/-)-t-butyl-3-[(Z)-(4-acetyl-5-benzyl-3,6-dioxopiperazin-2-ylidene)methyl]-4-nitroindole-1-carboxylate 
• 1235977-23-7 (+/-)-t-butyl-3-[(Z)-(4-acetyl-5-benzyl-3,6-dioxopiperazin-2-ylidene)methyl]indole-1-carboxylate 
• 23512-67-6 (+/-)-N-acetylglycylphenylalanine methyl ester 

Relevant academic research and scientific papers

Histamine H3 receptor antagonists with peptidomimetic (keto)piperazine structures to inhibit Aβ oligomerisation

Alzheime?s disease (AD) is the most prominent neurodegenerative disorder with high medical need. Protein-protein-interactions (PPI) interactions have a critical role in AD where β-amyloid structures (Aβ) build toxic oligomers. Design of disease modifying multi target directed ligand (MTDL) has been performed, which disable PPI on the one hand and on the other hand, act as procognitive antagonists at the histamine H3 receptor (H3R). The synthetized compounds are structurally based on peptidomimetic amino acid-like structures mainly as keto, diketo-, or acyl variations of a piperazine moiety connected to an H3R pharmacophore. Most of them showed low nanomolar affinities at H3R and some with promising affinity to Aβ-monomers. The structure–activity relationships (SAR) described offer new possibilities for MTDL with an optimized profile combining symptomatic and potential causal therapeutic approaches in AD.

The synthesis and biological activity of the 3-ferrocenylpropenamides derived from 5(4H)-oxazolones

We described a synthesis of new 3-ferrocenylpropenamides prepared by oxazolone-ring opening reaction with various primary and secondary amines. The antiproliferative activities of the obtained compounds were screened on human tumor cell lines (HCT116, SW6

Heterocyclic cellular lipid peroxidation inhibitors inspired by the marine antioxidant barettin

The marine environment remains a rich source for the discovery and development of novel bioactive compounds. The present paper describes the design, synthesis and biological evaluation of a library of small molecule heterocyclic mimetics of the marine 2,5

Site selective synthesis of cytotoxic 1,3,6-trisubstituted 3,6-diunsaturated (3Z,6Z)-2,5-diketopiperazines via a one-pot multicomponent method

A one-pot multicomponent approach was established for site selective synthesis of novel 1,3,6-trisubstituted 3,6-diunsaturated (3Z,6Z)-2,5-diketopiperazine derivatives with high stereoselectivity. The computational studies revealed that the steric hindran

Design and synthesis of novel soluble 2,5-diketopiperazine derivatives as potential anticancer agents

Non-protected 2,5-diketopiperazine derivatives have poor solubility thus with negative impact on their bioavailability. In the present study, twenty-one novel soluble mono-protected, and three non-protected 2,5-diketopiperazine derivatives were designed and synthesized. Their anticancer activity to ten cell lines were evaluated by using CCK8 assay, and the results showed that about half of the mono-protected derivatives had broad-spectrum anticancer activity. Among allyl-protected derivatives, compound 4m had strong activity to all the cell lines (IC50 = 0.5-4.5 μM), especially to the cancer cell lines U937 (IC50 = 0.5 μM) and K562 (IC50 = 0.9 μM). Compound 4m could become a lead compound for further development for anticancer agents.

Novel approach to the synthesis of aliphatic and aromatic α-keto acids

A new practical and efficient synthesis of α-keto acids was accomplished starting from the synthon 1,4-diacetylpiperazine-2,5-dione. The synthesis encompasses both aromatic and aliphatic substrates proving to be versatile and innovative with excellent carbon economy and recycling of the glycine by-product.

Synthesis and structure-activity relationship study of antimicrotubule agents phenylahistin derivatives with a didehydropiperazine-2,5-dione structure

Plinabulin (11, NPI-2358) is a potent microtubule-targeting agent derived from the natural diketopiperazine "phenylahistin" (1) with a colchicine-like tubulin depolymerization activity. Compound 11 was recently developed as VDA and is now under phase II clinical trials as an anticancer drug. To develop more potent antimicrotubule and cytotoxic derivatives based on the didehydro-DKP skeleton, we performed further modification on the tert-butyl or phenyl groups of 11, and evaluated their cytotoxic and tubulin-binding activities. In the SAR study, we developed more potent derivatives 33 with 2,5-difluorophenyl and 50 with a benzophenone in place of the phenyl group. The anti-HuVEC activity of 33 and 50 exhibited a lowest effective concentration of 2 and 1 nM for microtubule depolymerization, respectively. The values of 33 and 50 were 5 and 10 times more potent than that of CA-4, respectively. These derivatives could be a valuable second-generation derivative with both vascular disrupting and cytotoxic activities.

Synthesis and phytotoxicity of structural analogues of thaxtomin natural products

Structural analogues of the phytotoxic thaxtomin natural products have been synthesized by building upon a piperazinedione core and from l-phenylalanine. The compounds were evaluated for their phytotoxic activity against Arabidopsis thaliana seedlings and some of the key features for activity have been identified. CSIRO 2010.

ANALOGS OF DEHYDROPHENYLAHISTINS AND THEIR THEAPEUTIC USE

Compounds represented by the following structure (II) are disclosed: as are methods for making such compounds. Compositions and methods for treating various disease conditions including cancer and non-cancer diseases associated with vascular proliferation are also disclosed.

Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof

Compounds represented by the following structure (I) are disclosed: as are methods for making such compounds, wherein said methods comprise reacting a diacyldiketopiperazine with a first aldehyde to produce an intermediate compound; and reacting the intermediate compound with a second aldehyde to produce the class of compounds with the generic structure, where the first aldehyde and the second aldehydes are selected from the group consisting of an oxazolecarboxaldeyhyde, imidazolecarboxaldehyde, a benzaldehyde, imidazolecarboxaldehyde derivatives, and benzaldehyde derivatives, thereby forming the above compound wherein R1, R1′, R1″, R2, R3, R4, R5, and R6, X1 and X2, Y, Z, Z1, Z2, Z3, and Z4 may each be separately defined in a manner consistent with the accompanying description. Compositions and methods for treating vascular proliferation are also disclosed.