Page last updated: 2024-11-13

(6-chloro-1-(2-(dimethylamino)ethyl)indol-3-yl)-spiro(1h-isobenzofuran-3,4'-piperidine)-1'-yl-methanone

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Description

You are describing a complex chemical compound with the systematic name **(6-chloro-1-(2-(dimethylamino)ethyl)indol-3-yl)-spiro(1H-isobenzofuran-3,4'-piperidine)-1'-yl-methanone**.

Let's break down its structure and potential importance:

**Structure:**

* **Indole core:** The compound is built around an indole ring system, a common structure in many biologically active molecules.
* **Substitution:** The indole core is modified with a chlorine atom at the 6th position, a dimethylaminoethyl group at the 1st position, and a carbonyl group at the 3rd position.
* **Spirocyclic system:** The indole is connected through a spirocyclic system to a piperidine ring, which itself has a benzofuran moiety attached.
* **Ketone function:** The compound has a ketone functional group, which is known to participate in various biological interactions.

**Potential Importance in Research:**

Given its structure and complexity, this compound could have potential significance in several research areas:

* **Pharmacological activity:** The presence of the indole core and various functional groups suggests potential pharmacological activity. It could be investigated for:
* **Antidepressant properties:** Indoles are often associated with serotonin modulation, which is relevant to depression treatment.
* **Anti-inflammatory effects:** The benzofuran moiety has been linked to anti-inflammatory properties in some studies.
* **Other therapeutic applications:** The compound's complex structure might lead to unique interactions with biological targets, potentially yielding new drug leads.
* **Materials science:** Spirocyclic systems are often used in the design of new materials due to their structural rigidity and interesting optical properties.
* **Organic synthesis:** The compound's complex structure could be a valuable synthetic target, potentially leading to the development of new synthetic methodologies or building blocks for other complex molecules.

**Important Note:** It's crucial to remember that the potential importance of this compound is purely speculative based on its structure. Experimental studies are needed to determine its actual properties and biological activity.

(6-chloro-1-(2-(dimethylamino)ethyl)indol-3-yl)-spiro(1H-isobenzofuran-3,4'-piperidine)-1'-yl-methanone: a vasopressin 1a receptor antagonist; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID59657596
CHEMBL ID3416885
SCHEMBL ID4361592
SCHEMBL ID4361597
MeSH IDM000606701

Synonyms (25)

Synonym
SCHEMBL4361592
SCHEMBL4361597
CS-7944
HY-12981
rg7713
ro-5028442
ro5028442
bdbm50077217
CHEMBL3416885 ,
LZ0EU1YHCK ,
920022-47-5
unii-lz0eu1yhck
(6-chloro-1-(2-(dimethylamino)ethyl)indol-3-yl)-spiro(1h-isobenzofuran-3,4'-piperidine)-1'-yl-methanone
methanone, (6-chloro-1-(2-(dimethylamino)ethyl)-1h-indol-3-yl)spiro(isobenzofuran-1(3h),4'-piperidin)-1'-yl-
rg 7314
ro 5028442
DB12721
[6-chloro-1-[2-(dimethylamino)ethyl]indol-3-yl]-spiro[1h-2-benzofuran-3,4'-piperidine]-1'-ylmethanone
Q18392912
BCP32628
ro-5028442; ro 5028442;rg7713;rg-7713;rg 7713
N16810
MS-27852
AKOS037515536
VLB02247
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Vasopressin V1a receptorHomo sapiens (human)IC50 (µMol)0.00200.00060.38352.0000AID1721646; AID1820285
Vasopressin V1a receptorHomo sapiens (human)Ki0.00330.00020.62357.0300AID1200052; AID1426367; AID1721645; AID1820284
Vasopressin V1a receptorMus musculus (house mouse)Ki0.03900.03900.03900.0390AID1200055
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Vasopressin V1a receptorHomo sapiens (human)Kbapp0.00260.00260.00260.0026AID1200054
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (28)

Processvia Protein(s)Taxonomy
maternal aggressive behaviorVasopressin V1a receptorHomo sapiens (human)
positive regulation of systemic arterial blood pressureVasopressin V1a receptorHomo sapiens (human)
generation of precursor metabolites and energyVasopressin V1a receptorHomo sapiens (human)
activation of phospholipase C activityVasopressin V1a receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationVasopressin V1a receptorHomo sapiens (human)
negative regulation of female receptivityVasopressin V1a receptorHomo sapiens (human)
grooming behaviorVasopressin V1a receptorHomo sapiens (human)
blood circulationVasopressin V1a receptorHomo sapiens (human)
positive regulation of cell population proliferationVasopressin V1a receptorHomo sapiens (human)
positive regulation of heart rateVasopressin V1a receptorHomo sapiens (human)
positive regulation of glutamate secretionVasopressin V1a receptorHomo sapiens (human)
myotube differentiationVasopressin V1a receptorHomo sapiens (human)
calcium-mediated signalingVasopressin V1a receptorHomo sapiens (human)
telencephalon developmentVasopressin V1a receptorHomo sapiens (human)
positive regulation of cell growthVasopressin V1a receptorHomo sapiens (human)
positive regulation of prostaglandin biosynthetic processVasopressin V1a receptorHomo sapiens (human)
positive regulation of cellular pH reductionVasopressin V1a receptorHomo sapiens (human)
social behaviorVasopressin V1a receptorHomo sapiens (human)
cellular response to water deprivationVasopressin V1a receptorHomo sapiens (human)
maternal behaviorVasopressin V1a receptorHomo sapiens (human)
sperm ejaculationVasopressin V1a receptorHomo sapiens (human)
response to corticosteroneVasopressin V1a receptorHomo sapiens (human)
negative regulation of transmission of nerve impulseVasopressin V1a receptorHomo sapiens (human)
transport across blood-brain barrierVasopressin V1a receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayVasopressin V1a receptorHomo sapiens (human)
positive regulation of vasoconstrictionVasopressin V1a receptorHomo sapiens (human)
cellular response to hormone stimulusVasopressin V1a receptorHomo sapiens (human)
regulation of systemic arterial blood pressure by vasopressinVasopressin V1a receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
vasopressin receptor activityVasopressin V1a receptorHomo sapiens (human)
protein kinase C bindingVasopressin V1a receptorHomo sapiens (human)
protein bindingVasopressin V1a receptorHomo sapiens (human)
peptide hormone bindingVasopressin V1a receptorHomo sapiens (human)
V1A vasopressin receptor bindingVasopressin V1a receptorHomo sapiens (human)
peptide bindingVasopressin V1a receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
endosomeVasopressin V1a receptorHomo sapiens (human)
plasma membraneVasopressin V1a receptorHomo sapiens (human)
endocytic vesicleVasopressin V1a receptorHomo sapiens (human)
plasma membraneVasopressin V1a receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID1200060Solubility of the compound in phosphate buffer at pH 6.5 incubated for 1 hr with stirring followed by 2 hrs of shaking by Lysa assay2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Discovery of highly selective brain-penetrant vasopressin 1a antagonists for the potential treatment of autism via a chemogenomic and scaffold hopping approach.
AID1721645Displacement of [3H]AVP from human V1a receptor expressed in 1132N1 cells assessed as dissociation constant by radioligand binding assay2020Bioorganic & medicinal chemistry letters, 09-15, Volume: 30, Issue:18
New V1a receptor antagonist. Part 1. Synthesis and SAR development of urea derivatives.
AID1820294Displacement of [3H]-labelled arginine-vasopressin from human V2 receptor expressed in human 1321N1 cell membranes at 1 uM incubated for 60 mins by radioligand binding assay2021Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14
Synthesis and Characterization of New V
AID1200054Antagonist activity at human vasopressin 1a receptor expressed in CHO cells assessed as inhibition of vasopressin-induced calcium flux preincubated for 20 mins followed by vasopressin induction measured for 5 mins by FLIPR assay2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Discovery of highly selective brain-penetrant vasopressin 1a antagonists for the potential treatment of autism via a chemogenomic and scaffold hopping approach.
AID1721653Efflux ratio of Apparent permeability across apical to basolateral side in human Caco-2 cells at 10 uM by HPLC-UV or UHPLC-MS/MS analysis2020Bioorganic & medicinal chemistry letters, 09-15, Volume: 30, Issue:18
New V1a receptor antagonist. Part 1. Synthesis and SAR development of urea derivatives.
AID1820285Inhibition of human V1A receptor expressed in human 1321N1 cells assessed as calcium mobilization by fluorescent plate reader2021Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14
Synthesis and Characterization of New V
AID1200063Volume of distribution at steady state in mouse at 2 mg/kg, iv2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Discovery of highly selective brain-penetrant vasopressin 1a antagonists for the potential treatment of autism via a chemogenomic and scaffold hopping approach.
AID1200058Selectivity ratio of Ki for human vasopressin V2 receptor to Ki for human vasopressin 1a receptor2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Discovery of highly selective brain-penetrant vasopressin 1a antagonists for the potential treatment of autism via a chemogenomic and scaffold hopping approach.
AID1721646Antagonist activity at human V1a receptor expressed in human 1321N1 cells assessed as decrease in Arg8-vasopressin-stimulated calcium flux by fluorometric calcium assay2020Bioorganic & medicinal chemistry letters, 09-15, Volume: 30, Issue:18
New V1a receptor antagonist. Part 1. Synthesis and SAR development of urea derivatives.
AID1200064Clearance in mouse at 2 mg/kg, iv2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Discovery of highly selective brain-penetrant vasopressin 1a antagonists for the potential treatment of autism via a chemogenomic and scaffold hopping approach.
AID1820284Displacement of [3H]-arginine-vasopressin from human V1A receptor expressed in human 1321N1 cell membranes incubated for 60 mins by radioligand binding assay2021Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14
Synthesis and Characterization of New V
AID1200055Displacement of [3H]-vasopressin from mouse vasopressin 1a receptor expressed in HEK293 cell membranes after 1 hr by scintillation proximity assay2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Discovery of highly selective brain-penetrant vasopressin 1a antagonists for the potential treatment of autism via a chemogenomic and scaffold hopping approach.
AID1721647Metabolic stability in human liver microsomes assessed as intrinsic clearance at 1 uM in presence of NADPH by HPLC-UV analysis2020Bioorganic & medicinal chemistry letters, 09-15, Volume: 30, Issue:18
New V1a receptor antagonist. Part 1. Synthesis and SAR development of urea derivatives.
AID1200052Displacement of [3H]-vasopressin from human vasopressin 1a receptor expressed in HEK293 cell membranes after 1 hr by scintillation proximity assay2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Discovery of highly selective brain-penetrant vasopressin 1a antagonists for the potential treatment of autism via a chemogenomic and scaffold hopping approach.
AID1560508Half life in iv dosed human2020Journal of medicinal chemistry, 02-27, Volume: 63, Issue:4
Discovery of Balovaptan, a Vasopressin 1a Receptor Antagonist for the Treatment of Autism Spectrum Disorder.
AID1200061Activity at human P-gp assessed as drug transport2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Discovery of highly selective brain-penetrant vasopressin 1a antagonists for the potential treatment of autism via a chemogenomic and scaffold hopping approach.
AID1200062Ratio of drug level in brain to plasma in mouse at 10 mg/kg, po2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Discovery of highly selective brain-penetrant vasopressin 1a antagonists for the potential treatment of autism via a chemogenomic and scaffold hopping approach.
AID1721651Apparent permeability across apical to basolateral side in human Caco-2 cells at 10 uM by HPLC-UV or UHPLC-MS/MS analysis2020Bioorganic & medicinal chemistry letters, 09-15, Volume: 30, Issue:18
New V1a receptor antagonist. Part 1. Synthesis and SAR development of urea derivatives.
AID1721648Metabolic stability in Wistar rat liver microsomes assessed as intrinsic clearance at 1 uM in presence of NADPH by HPLC-UV analysis2020Bioorganic & medicinal chemistry letters, 09-15, Volume: 30, Issue:18
New V1a receptor antagonist. Part 1. Synthesis and SAR development of urea derivatives.
AID1721649Metabolic stability in NMRI mouse liver microsomes assessed as intrinsic clearance at 1 uM in presence of NADPH by HPLC-UV analysis2020Bioorganic & medicinal chemistry letters, 09-15, Volume: 30, Issue:18
New V1a receptor antagonist. Part 1. Synthesis and SAR development of urea derivatives.
AID1200059Selectivity ratio of Ki for human oxytocin receptor to Ki for human vasopressin 1a receptor2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Discovery of highly selective brain-penetrant vasopressin 1a antagonists for the potential treatment of autism via a chemogenomic and scaffold hopping approach.
AID1426367Antagonist activity at human vasopressin 1a receptor2017Journal of medicinal chemistry, 02-23, Volume: 60, Issue:4
Recent Advances in Scaffold Hopping.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's3 (50.00)24.3611
2020's3 (50.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.49

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.49 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.49)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (16.67%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]