Category: 137419-24-0

Tantry, Subramanyam J. published the artcileWhole cell screen based identification of spiropiperidines with potent antitubercular properties, Recommanded Product: tert-Butyl spiro[indene-1,4′-piperidine]-1′-carboxylate, the main research area is spiropiperidine antitubercular; Antimycobacterial; Hypoxic conditions; MmpL3; Non-replicating phase; Whole cell screen; ss18b.

Whole cell based screens to identify hits against Mycobacterium tuberculosis (Mtb), carried out under replicating and non-replicating (NRP) conditions, resulted in the identification of multiple, novel but structurally related spiropiperidines with potent antitubercular properties. These compounds could be further classified into three classes, namely, 3-(3-aryl-1,2,4-oxadiazol-5-yl)-1′-alkylspiro[indene-1,4′-piperidine] (abbr. spiroindenes), 4-(3-aryl-1,2,4-oxadiazol-5-yl)-1′-alkylspiro[chromene-2,4′-piperidine] (abbr. spirochromenes) and 1′-benzylspiro[indole-1,4′-piperidin]-2(1H)-one (abbr. spiroindolones). Spiroindenes showed ≥4 log10 kill (at 2-12 μM) on replicating Mtb, but were moderately active under non replicating conditions. Whole genome sequencing efforts of spiroindene-resistant mutants resulted in the identification of the I292L mutation in MmpL3 (Mycobacterial membrane protein Large), required for the assembly of mycolic acid into the cell wall core of Mtb. MIC modulation studies demonstrated that the mutants were cross-resistant to spirochromenes but not to spiroindolones. This paper describes lead identification efforts to improve potency while reducing the lipophilicity and hERG liabilities of spiroindenes. Addnl., as deduced from the SAR studies, the authors provide insights regarding the new chem. opportunities that the spiroindolones can offer to the TB drug discovery initiatives.

Bioorganic & Medicinal Chemistry Letters published new progress about Mutation. 137419-24-0 belongs to class piperidines, name is tert-Butyl spiro[indene-1,4′-piperidine]-1′-carboxylate, and the molecular formula is C18H23NO2, Recommanded Product: tert-Butyl spiro[indene-1,4′-piperidine]-1′-carboxylate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Agarwal, Jyoti published the artcileWater-mediated, highly-efficient and improved protocol for the synthesis of vesamicol, its analogues and β-blockers through the highly-chemoselective aminolysis of epoxides, COA of Formula: C18H23NO2, the main research area is vesamicol analog green preparation diastereoselective; epoxide aryl piperidine chemoselective aminolysis water mediated.

An efficient, eco-friendly and cost-effective protocol was developed for the synthesis of vesamicol e.g., I, benzovesamicol, spirovesamicol, their analogs and drug mols. such as Naftopidil and SR 59230 A. In this reaction, water had played dual role i.e. of bifunctional catalyst and reaction medium, also no other chem. reagent/promotor was required to afford the products. Reaction follows 100% atom economy and was found to be highly chemo-selective. All studied reactions worked well to yield the corresponding products in excellent to near quant. yields without following the tedious and time consuming column chromatog. as purification step. Thus, this protocol provided the vesamicol and other products without generating any chem. waste to the environment.

ChemistrySelect published new progress about Aminolysis. 137419-24-0 belongs to class piperidines, name is tert-Butyl spiro[indene-1,4′-piperidine]-1′-carboxylate, and the molecular formula is C18H23NO2, COA of Formula: C18H23NO2.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chambers, Mark S. published the artcileSpiropiperidines as high-affinity, selective σ ligands., HPLC of Formula: 137419-24-0, the main research area is spiropiperidine selective sigma ligand; tetralin spiropiperidino selective sigma ligand; indan spiropiperidino selective sigma ligand; benzocycloheptane spiropiperidino selective sigma ligand; radioligand displacement spiropiperidinobenzocycloalkane; structure activity spiropiperidinobenzocycloalkane receptor binding.

A variety of achiral conformationally restricted spirocyclic piperidines were prepared in an attempt to investigate the functional role of the central σ recognition site. All compounds possessed a lipophilic N-substituent incorporating either a tetralin (I; n = 2, R = PhCH2, Bu, hexyl, 2-picolyl, cyclohexylmethyl, CH2CH:CH2, 2-furylmethyl, 2-thienylmethyl, CH2CH:CMe2, etc.), indan (I; n = 1, R = PhCH2, PhCH2CH2, CH2CH:CMe2, Bu, etc.), or benzocycloheptane skeleton (I; n = 3, R = PhCH2, Bu). Their in vitro affinity at the σ site was assessed in radioligand displacement experiments with guinea pig cerebellum homogenates using the σ-specific radioligand N,N-di-o-[5-3H]-tolylguanidine (II). A study of the structure-activity relationships identified the N-Bu and N-dimethylallyl substituents as the optimum groups for high affinity and selectivity at the σ site, e.g., I (n = 1, R = CH2CH:CMe2), pIC50 = 8.9 vs II and >10,000-fold selective over the dopamine D2 receptor. Such compounds are amongst the highest affinity σ ligands reported to date, with excellent selectivity over the dopamine D2 receptor, and may serve as a useful tool for exploring the physiol. role of the σ site.

Journal of Medicinal Chemistry published new progress about Antipsychotics. 137419-24-0 belongs to class piperidines, name is tert-Butyl spiro[indene-1,4′-piperidine]-1′-carboxylate, and the molecular formula is C18H23NO2, HPLC of Formula: 137419-24-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Tata, James R. published the artcileThe synthesis and activity of spiroindane growth hormone secretagogues, Synthetic Route of 137419-24-0, the main research area is spiroindane preparation growth hormone secretagogue structure.

The synthesis and activities of a series of spiroindane growth hormone secretagogues is reported. Modification of the benzylic position of the spiroindane has resulted in a dramatic increase in potency resulting in sub-nanomolar peptidomimetic growth hormone secretagogues. In vivo data demonstrating the good oral activity of these analogs is reported.

Bioorganic & Medicinal Chemistry Letters published new progress about Structure-activity relationship. 137419-24-0 belongs to class piperidines, name is tert-Butyl spiro[indene-1,4′-piperidine]-1′-carboxylate, and the molecular formula is C18H23NO2, Synthetic Route of 137419-24-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Ohrui, Sayaka published the artcileDesign and synthesis of novel orexin antagonists via structural simplification of the morphinan skeleton, Product Details of C18H23NO2, the main research area is orexin ligand spiro piperidine antagonist preparation.

Herein, novel orexin antagonists with a spiro-type piperidine skeleton was designed and synthesized via removal of the unnecessary sites of orexin 1 receptor (OX1R) antagonists with a morphinan skeleton for binding to OX1R. In addition, while decahydroisoquinoline compounds with an A-ring did not show antagonistic activity for OX1R, spiro-type piperidine compounds with a dihydroindene structure showed antagonistic activities. This suggests that the lipophilic site corresponding to the A-ring of the morphinan skeleton is important for determining the antagonistic activity toward OX1R.

Heterocycles published new progress about Diastereoselective synthesis. 137419-24-0 belongs to class piperidines, name is tert-Butyl spiro[indene-1,4′-piperidine]-1′-carboxylate, and the molecular formula is C18H23NO2, Product Details of C18H23NO2.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Takemoto, Toshiyasu published the artcileAsymmetric synthesis of enantiomerically pure spiro [((2S)-hydroxy)indane-1,4′-piperidine], Quality Control of 137419-24-0, the main research area is spirohydroxyindanepiperidine enantioselective preparation intermediate tachykinin receptor antagonist; asym synthesis enantiomerically pure spirohydroxyindanepiperidine.

Two methods for the preparation of enantiomerically pure spirohydroxyindanepiperidine (S)-I (R = H), a key intermediate for the synthesis of a tachykinin receptor antagonist, from indenepiperidine II (R = H) are described. E.g., II (R = Me3COCO, Boc) was epoxidized with methyltrioxorhenium, the epoxide opened regioselectively to the 2-indanone derivative which was oxidized with PCC and then reduced enantioselectively in the presence of an Corey-Bakshi-Shibata oxazaborolidine catalyst to give N-Boc (S)-I (R = Boc) in 100% yield and 89% ee from the 2-indanone derivative E.g., II (R = Boc) was epoxidized enantioselectively with the (R,R)-Jacobsen epoxidation catalyst to give epoxide III in 51% yield and 91% ee; III was reduced regioselectively with ammonium formate in the presence of palladium on carbon, and the Boc derivative was then deprotected with HCl in dioxane to give the hydrochloride salt of I (R = H).

Tetrahedron: Asymmetry published new progress about Epoxidation, stereoselective. 137419-24-0 belongs to class piperidines, name is tert-Butyl spiro[indene-1,4′-piperidine]-1′-carboxylate, and the molecular formula is C18H23NO2, Quality Control of 137419-24-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chen, Xiaoqi published the artcileDiscovery and characterization of a potent and selective antagonist of melanin-concentrating hormone receptor 2, Computed Properties of 137419-24-0, the main research area is MCHR 2 antagonist carbazolylmethyl spiroindanpiperidine preparation.

A series of carbazoylylmethylindanspiropiperidines were synthesized and evaluated as MCHR2 antagonists using a FLIPR assay. The pharmacokinetic properties of selected compounds have also been studied. This effort led to the discovery of potent and specific MCHR2 antagonists. Thus, I demonstrated good pharmacokinetic properties across rat, beagle dog and rhesus monkey and had a favorable selectivity profile against a number of other receptors. These MCHR2 antagonists are considered appropriate tool compounds for study of the function of MCHR2 in vivo.

Bioorganic & Medicinal Chemistry Letters published new progress about. 137419-24-0 belongs to class piperidines, name is tert-Butyl spiro[indene-1,4′-piperidine]-1′-carboxylate, and the molecular formula is C18H23NO2, Computed Properties of 137419-24-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem