tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate

• CAS: 896464-16-7
• Catalog Number: ACM896464167
• Category: Main Products
• Molecular Weight: 226.32
• Molecular Formula: C12H22N2O2
• Boiling Point: 319 °C
• Flash Point: 147 °C

Case Study

tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate as a Key Building Block for Ghrelin Receptor Inverse Agonists

Daina, Antoine, et al. Journal of medicinal chemistry 61.24 (2018): 11039-11060.

The ghrelin receptor (GHSR) is a promising therapeutic target for obesity and type-2 diabetes, given its role in regulating food intake and glucose homeostasis. Inverse agonists of GHSR offer potential advantages over neutral antagonists by suppressing constitutive receptor activity. In this study, tert-butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate was employed as a strategic spirocyclic scaffold in the design of novel GHSR modulators through chimeric hybridization of known inverse agonist PF-05190457 and antagonist H0700.
Synthesis: The spirocyclic amine building block was prepared and subjected to reductive amination with 5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-one, followed by chiral separation, Boc-deprotection, and urea formation with functionalized benzylamines to generate target compounds 9 and 10.
Key Results: The spirocyclic scaffold successfully combined structural elements from both parent molecules, yielding compounds with GHSR inverse agonist activity. Compound 9 (R = pyrazinyl) exhibited potent inverse agonism (IP-1 EC50 = 483 nM) and antagonism (FLIPR IC50 = 1210 nM), while compound 10 (R = H) showed reduced activity (IC50 = 4010 nM, inactive in IP-1), demonstrating the importance of the pyrazinyl substituent. Subsequent optimization of related piperidine-based analogs led to compound 47, a potent GHSR inverse agonist (IP-1 EC50 = 29 nM) with moderate oral bioavailability (F = 27%) and significant brain penetration (B/P ratio = 1.86), demonstrating the utility of this building block approach.

Custom Q&A

What is the molecular formula of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate?

The molecular formula of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate is C12H22N2O2.

What are the synonyms for tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate?

The synonyms for tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate are 7-Boc-2,7-diaza-spiro[3.5]nonane and 2,7-Diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester.

What is the molecular weight of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate?

The molecular weight of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate is 226.32 g/mol.

When was tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate created?

tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate was created on June 26, 2008.

What is the InChI of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate?

The InChI of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate is InChI=1S/C12H22N2O2/c1-11(2,3)16-10(15)14-6-4-12(5-7-14)8-13-9-12/h13H,4-9H2,1-3H3.

What is the InChIKey of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate?

The InChIKey of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate is NRADOPGBTAJXKB-UHFFFAOYSA-N.

What is the Canonical SMILES of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate?

The Canonical SMILES of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate is CC(C)(C)OC(=O)N1CCC2(CC1)CNC2.

What is the CAS number of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate?

The CAS number of tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate is 896464-16-7.

How many hydrogen bond donor counts are there in tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate?

There is 1 hydrogen bond donor count in tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate.

How many hydrogen bond acceptor counts are there in tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate?

There are 3 hydrogen bond acceptor counts in tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate.

Synthetic Use

Downstream Synthesis Route 1

• 624-28-2
• 896464-16-7

• 1032158-27-2

Reference: [1]Patent: WO2008/68265,2008,A1 .Location in patent: Page/Page column 38

Downstream Synthesis Route 2

• 896464-16-7
• 959960-89-5

• 1032158-36-3

Reference: [1]Patent: WO2008/68265,2008,A1 .Location in patent: Page/Page column 41-42

* For details of the synthesis route, please refer to the original source to ensure accuracy.