16655-71-3

Basic information

• Product Name: 2-(indanyl)glycine
• Synonyms: 2-(indanyl)glycine
• CAS NO: 16655-71-3
• Molecular Formula: C11H13 N O2
• Molecular Weight: 0
• Mol File: 16655-71-3.mol

Chemical Properties

• Boiling Point: 372.9°Cat760mmHg
• Flash Point: 179.3°C
• Appearance: /
• Density: 1.254g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: 2-(indanyl)glycine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(indanyl)glycine(16655-71-3)
• EPA Substance Registry System: 2-(indanyl)glycine(16655-71-3)

Safety Data

• Hazardous Substances Data: 16655-71-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13NO2/c12-10(11(13)14)9-6-5-7-3-1-2-4-8(7)9/h1-4,9-10H,5-6,12H2,(H,13,14)

Upstream product

• 37414-44-1 indan-2-carbaldehyde 
• 114915-75-2 1-oxoindan-Δ^2,α-acetic acid 
• 16655-90-6 amino(2,3-dihydro-1H-inden-2-yl)ethanoic acid 
• 24329-96-2 2-iodoindane 
• 870151-48-7 tert-butyl N-(diphenylmethylene)-2-(2-indanyl)glycinate 
• 216222-68-3 rac-indanylglycine hydantoin 
• 870151-49-8 (R)-N-carbamylindanylglycine 
• 847153-94-0 (R)-((R)-1-Oxo-indan-2-yl)-((R)-1-phenyl-ethylamino)-acetic acid 
• 155172-72-8 methyl 2-(2-indanyl)glycinate hydrochloride 

Downstream Products

• 181227-48-5 (2R)-[(t-butoxycarbonyl)amino](2,3-dihydro-1H-inden-2-yl)ethanoic acid 
• 181227-46-3 (2R)-amino(2,3-dihydro-1H-inden-2-yl)ethanoic acid 

Relevant articles and documents

Method for preparing D-indanyl glycine

The invention discloses a method for preparing D-indanyl glycine. The method specifically comprises the following steps: dissolving 2-indan aldehyde, R-2-hydroxylamino-2-phenylethanol in a mixed solution of ethanol and water or an organic solvent A, and stirring at the temperature of 10-40 DEG C to be completely reacted so as to obtain a compound I; dissolving the obtained compound I and trimethylsilyl cyanide in an organic solvent B, reacting at the temperature of 0-70 DEG C in the presence of a catalyst A for 1-8 hours so as to obtain a compound II; mixing the obtained compound II and an acid, and carrying out a hydrolysis reaction at the temperature of 30-120 DEG C for 1-10 hours so as to obtain a compound III; and dissolving the obtained compound III in an organic solvent C, adding a catalyst B, carrying out an atmospheric hydrogenation reaction at the temperature of 40-60 DEG C for 4-12 hours, and filtering the obtained product to remove the catalyst B, thereby obtaining the D-indanyl glycine. The method disclosed by the invention has the advantages of mild reaction conditions, easy and convenient operation, high atom utilization rate, environmental friendliness, low production cost and the like, and is a novel method for preparing the D-indanyl glycine.

Preparation method of R-2-dihydroindenyl glycine

The invention discloses a novel method for preparing R-2-dihydroindenyl glycine. The preparation method comprises the following steps of making 2-dihydroindenyl aldehyde, D-phenylglycinol and trimethylsilyl cyanide subjected to an asymmetric cyanosilylation reaction under the action of a catalyst A, and afterwards, making a first reaction product subjected to post treatment to obtain a compound I shown by a formula (I); hydrolyzing the compound I shown by the formula (I) in an acidic condition, making a second reaction product subjected to post treatment to obtain a compound II shown by a formula II; afterwards, making the compound II shown by the formula (II) subjected to a catalytic hydrogenation reaction to obtain the R-2-dihydroindenyl glycine shown by a formula (III). Cheap and easily-obtained organic raw materials are utilized for the novel method; the preparation method has the advantages of being mild in reaction conditions, being simple and convenient to operate, being high in atomic utilization rate, being environment-friendly and being low in production cost, and the like.

Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: Synthesis, pharmacokinetics, and in vivo potency

A six-stage stereoselective synthesis of indanyl-7-(3′-pyridyl)-(3R, 6R,7R)-2,5-diketopiperazines oxytocin antagonists from indene is described. SAR studies involving mono- and disubstitution in the 3′-pyridyl ring and variation of the 3-isobutyl group gave potent compounds (pKi > 9.0) with good aqueous solubility. Evaluation of the pharmacokinetic profile in the rat, dog, and cynomolgus monkey of those derivatives with low cynomolgus monkey and human intrinsic clearance gave 2′,6′-dimethyl-3′- pyridyl R-sec-butyl morpholine amide Epelsiban (69), a highly potent oxytocin antagonist (pKi = 9.9) with >31000-fold selectivity over all three human vasopressin receptors hV1aR, hV2R, and hV1bR, with no significant P450 inhibition. Epelsiban has low levels of intrinsic clearance against the microsomes of four species, good bioavailability (55%) and comparable potency to atosiban in the rat, but is 100-fold more potent than the latter in vitro and was negative in the genotoxicity screens with a satisfactory oral safety profile in female rats.

2,5-Diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists. 2. Synthesis, chirality, and pharmacokinetics

A short stereoselective synthesis of a series of chiral 7-aryl-2,5-diketopiperazines oxytocin antagonists is described. Varying the functionality and substitution pattern of substituents in the 7-aryl ring and varying the chirality of this exocyclic ring have produced potent oxytocin antagonists (pKi > 8.5). SAR and pharmacokinetic profiling of this series of (3R,6R,7R)-2,5-diketopiperazines together with the introduction of an ortho F group in the 7-aryl ring to improve rat pK has culminated in the 2′,4′-difluorophenyldiketopiperazine derivative 37, a highly potent oxytocin antagonist against the human oxytocin receptor (pKi = 8.9) that has > 1000-fold selectivity over all three vasopressin receptors V1a, V2, and V1b. It has good bioavailability (46%) in the rat and moderate bioavailability (13-31%) in the dog and is more active in vivo in the rat than atosiban (rat DR10 = 0.44 mg/kg iv).

Crystallization-induced asymmetric transformation (CIAT) with simultaneous epimerization at two stereocenters. A short synthesis of conformationally constrained homophenylalanines

CIAT of aza-Michael adducts allows simultaneous build up of two stereocenters. A consequent short and efficient synthesis affords simple access to the both antipodes of various conformationally restricted homophenylalanines.

Enantioselective syntheses of homophenylalanine derivatives via nitrone 1,3-dipolar cycloaddition reactions with styrenes

A new two-step route to derivatives of homophenylalanine is presented. Cycloaddition of a cyclic nitrone glycine template with various styrene derivatives affords good yields of 5-substituted cycloadducts. One-step hydrogenolysis (three bonds) then affords the optically pure α-amino acids related to homophenylalanine.

Design and Synthesis of Side-Chain Conformationally Restricted Phenylalanines and Their Use for Structure-Activity Studies on Tachykinin NK-1 Receptor

Constrained analogues of phenylalanine have been conceptually designed for analyzing the binding pockets of Phe7 (S7) and Phe8 (S8), two aromatic residues important for the pharmacological properties of SP, i.e., L-tetrahydroisoquinoleic acid, L-diphenylalanine, L-9-fluorenylglycine (Flg), 2-indanylglycine, the diastreomers of L-1-indanylglycine (Ing) and L-1-benzindanylglycine (Bfi), and the Z and E isomers of dehydrophenylalanine (ΔZPhe, ΔEPhe).Binding studies were performed with appropriate ligands and tissue preparations allowing the discrimination of the three tachykinin binding sites, NK-1, NK-2, and NK-3.The potencies of these agonists were evaluated in the guinea pig ileum bioassay.According to the binding data, we can conclude that the S7 subsite is small, only the gauche(-) probe 7>SP presents a high affinity for specific NK-1 binding sites.Surprisingly, the EPhe7>SP analogue, which projects the aromatic ring toward the trans orientation, is over 40-fold more potent than the Z isomer, ZPhe7>SP.A plausible explanation of these conflictual results is that either the binding protein quenches the minor trans rotamer of 7>SP in solution or this constrained amino acid side chain rotates when inserted in the protein.In position 8, the high binding affinities of 8>SP and 8>SP suggest that the S8 subsite is large enough to accept two aromatic rings in the gauche(-) and one aromatic ring in the trans direction.Peptides bearing two conformational probes in positions 7, 8 or 9 led to postulate that S7, S8, and S9 subsites are independent from each other.The volumes available for side chains 7 and 8 can be estimated to be close to 110 and 240 Angstroem3, respectively.The large volume of the S8 subsite raises question on the localization of the SP-binding site in the NK-1 receptor.If SP were to bind in the transmembrane domains, the cleft defined by the seven transmembrane segments must rearrange during the binding process in order to bind a peptide in an α-helical structure and at least one large binding subsite in position 8.Thus, indirect topographical analysis with constrained amino acids might contribute to the analysis of the receptor/ligand dynamics.Finally, this study demonstrates that a good knowledge of the peptidic backbone structure and a combination of constrained amino acids are prerequisites to confidently attribute the preferred orientation(s) of an amino acid side chain.