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Design, synthesis and antitumor study of a series of N-Cyclic sulfamoylaminoethyl substituted 1,2,5-oxadiazol-3-amines as new indoleamine 2, 3-dioxygenase 1 (IDO1) inhibitors

Indoleamine 2, 3-dioxygenase 1 (IDO1) plays a key role in tryptophan catabolism which is an important mechanism in immune tolerance. The small molecule epacadostat is the most advanced IDO1 inhibitor, but its phase III trials as a single agent or in combinations with PD-1 antibody failed to show appreciable objective responses. To gain more insight on the antitumor efficacy of IDO1 inhibitors, we have designed a series of analogues of epacadostat by incorporating a cyclic aminosulfonamide moiety as the sidechain capping functionality. Compound 5a was found to display significant potency against recombinant hIDO1 and hIDO1 expressed HEK293 cancer cells. This compound has improved physico-chemical properties, acceptable PK parameters as well as optimal cardiac safety. Similar to epacadostat, 5a is ineffective as single agent in the CT-26 syngeneic xenograft model, however, the combination of 5a with PD-1 antibody showed both elevated tumor growth inhibition and prolonged median life span.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H429NO – PubChem

 

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Processes for the production of heterocyclic compounds

A ketonic heterocyclic compound having at least two heteroatoms in the ring is prepared by reacting a difunctional compound having the general formula STR1 in which R1, R2, R3 and R4 are members of the group consisting of aliphatic, aromatic, cycloaliphatic and heterocyclic hydrocarbons which may contain functional groups selected from –OH, –OR5, –COOH, –COOR5, –CN, –Cl, –Br, –I, –F, and –CO–R5, wherein R5 is an aliphatic, aromatic, cycloaliphatic or heterocyclic hydrocarbon; X is oxygen or sulphur; Y is sulphur or nitrogen; n is an integer ranging from 1 to 3, or zero; R6 is a hydrogen or a hydrocarbon radical included in the above definition of R1 R2 R3 and R4 ; and m is the valence of Y, with carbon monoxide and oxygen in the presence of a catalyst selected from selenium, selenium compounds and complexes of copper, in the temperature range of from room temperature to 80 C and in the pressure range of from 1 to 10 atmospheres.

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Oxazolidine – Wikipedia,
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Gold(I)-catalyzed intramolecular tandem addition/Friedel – Crafts reactions between acyclic enamides and 1-arylalkynes

Electron-deficient acyclic enamine derivatives react with electron-rich 1-arylalkynes using cationic gold(I) species as catalysts in an intramolecular process to form annulated 1-amido-substituted indene derivatives as the major products. Yields for this process range between 21% and 98%. In some cases, a two-step process that includes a subsequent alkene isomerization is needed.

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Oxazolidine – Wikipedia,
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Process for the manufacture of alkyl compounds

Process for the manufacture of a compound of formula I wherein R1 is H, acyl, alkyl or carbamoyl, R2 is a linear alkyl or alkenyl group, preferably a linear alkyl group comprising from 6 to 20 carbon atoms and n is 0, 1, 2, or 3, which comprises reacting a compound of formula II wherein R1 and n are as above and X is a leaving group with a carbanionic reagent of formula II ???????? M-R2 wherein R2 is as above and M denotes a metal or a metal containing group.

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Recent progress in the discovery and development of DNA gyrase B inhibitors

New antibacterials that modulate less explored targets are needed to fight the emerging bacterial resistance. DNA gyrase and topoisomerase IV are attractive targets in this search. These are both type II topoisomerases that can cleave both DNA strands, and can thus alter DNA topology during replication or similar processes. Currently, there are no ATP-competitive inhibitors of these two enzymes on the market, as the only aminocoumarin representative, novobiocin, was withdrawn due to safety concerns. The search for novel ATP-competitive inhibitors is a focus of ongoing industrial and academical research. This review summarizes the recent efforts in the design, synthesis and evaluation of GyrB/ParE inhibitors. The various approaches to achieve improved antibacterial activities are described, with particular reference to Gram-negative bacteria.

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Method of treating cancer

The present invention relates to methods of treating cancer using a combination of a compound which is an antineoplastic agent and a compound which is a inhibitor of prenyl-protein transferase, which methods comprise administering to said mammal, either sequentially in any order or simultaneously, amounts of at least two therapeutic agents selected from a group consisting of a compound which is an antineoplastic agent and a compound which is a inhibitor of prenyl-protein transferase. The invention also relates to methods of preparing such compositions.

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Hypervalent organoantimony and -bismuth compounds with pendant arm ligands

Recent developments in chemistry of hypervalent organoantimony and -bismuth complexes with bidentate (C,E)- and tridentate (E,C,E)- and (C,E,C)-ligands are reviewed. The ligands are bonded to the antimony or bismuth atoms through carbon atoms and through intramolecular coordination with dative bonds from nitrogen, oxygen or sulfur atoms. Syntheses, structures including chirality aspects, reactions, fluxional behavior, biological aspects and applications in the field of catalysis and organic syntheses are considered in this review.

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A Robust One-Step Approach to Ynamides

A robust one-step synthetic strategy for ynamide with cheap and easily available stock chemicals vinyl dichlorides and electron deficient amides as the starting material is described. In the absence of transition-metal catalyst, the reaction proceeds under mild reaction conditions in open air and thus rendering a convenient operation. This strategy is not only suitable for both terminal and internal ynamide synthesis but also amenable for large-scale preparation. Broad substrate scopes with respect to vinyl dichloride as well as electron-deficient amide were observed.

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Inverse Electron-Demand [4 + 2]-Cycloadditions of Ynamides: Access to Novel Pyridine Scaffolds

Functionalized polycyclic aminopyridines are central to the chemical sciences, but their syntheses are still hampered by a number of shortcomings. These nitrogenated heterocycles can be efficiently prepared by an intramolecular inverse electron demand hetero Diels-Alder (ihDA) cycloaddition of ynamides to pyrimidines. This ihDA/rDA sequence is general in scope and affords expedient access to novel types of aminopyridinyl scaffolds that hold great promise in terms of exit vector patterns.

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Oxazolidine – Wikipedia,
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A green synthetic route to imides from terminal alkynes and amides by simple solid catalysts

An atom-efficient and green synthetic route to highly valuable imides (5492% yields) from terminal alkynes and amides has been developed. This new route is composed of two consecutive reactions, that is, (i) the reported Cu(OH)2-catalyzed cross-coupling of terminal alkynes and amides to ynamides and (ii) the SnWmixed oxide-catalyzed regioselective hydration of ynamides.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H666NO – PubChem