BI 187004 , CAS No.1303515-32-3

CAS: 1303515-32-3 Cat. No.: B1439893 分子式: C₂₁H₁₈N₄O 分子量: 342.4 PubChem CID: 67223373

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

概要

BI 187004 (VTP-34072) is an 11β-hydroxysteroid dehydrogenase 1 inhibitor for use in diabetes research.

Specifications

保管条件

Store at -20°C

入荷

Ice chest + Ice pads

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

製品の性質

ALogP

3

名前と識別子

カノニカル・スマイル

C1CC2C(CC3=C2C=C(C=C3)C#N)N(C1)C(=O)C4=CC5=C(C=C4)N=CN5

IUPAC Name

(4aR,9aS)-1-(3H-benzimidazole-5-carbonyl)-2,3,4,4a,9,9a-hexahydroindeno[2,1-b]pyridine-6-carbonitrile

InChIKey

VVZNCSHIBODHMZ-UZLBHIALSA-N

INCHI

1S/C21H18N4O/c22-11-13-3-4-14-10-20-16(17(14)8-13)2-1-7-25(20)21(26)15-5-6-18-19(9-15)24-12-23-18/h3-6,8-9,12,16,20H,1-2,7,10H2,(H,23,24)/t16-,20+/m1/s1

異性体SMILES

C1C[C@H]2[C@H](CC3=C2C=C(C=C3)C#N)N(C1)C(=O)C4=CC5=C(C=C4)N=CN5

代替CAS番号

1303515-32-3

PubChem CID

67223373

分子量

342.4

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • 分類 Piperidines
      • Subclass N-acylpiperidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• 分類: Piperidines
• Subclass: N-acylpiperidines
• Intermediate Tree Nodes: Not available
• Direct Parent: N-benzoylpiperidines
• Alternative Parents: Indanes Benzimidazoles Tertiary carboxylic acid amides Imidazoles Heteroaromatic compounds Nitriles Azacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: N-benzoylpiperidine - Benzimidazole - Indane - Benzenoid - Azole - Imidazole - Tertiary carboxylic acid amide - Heteroaromatic compound - Carboxamide group - Nitrile - Carbonitrile - Carboxylic acid derivative - Azacycle - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Cyanide - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• 説明: This compound belongs to the class of organic compounds known as n-benzoylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Application Protocols

No tested application protocols are provided for this product. The following are general, non-binding suggestions for handling small-molecule tool compounds in biochemical or cellular assays.

Biochemical enzyme assay (general outline):

• Prepare a 10–50 mM DMSO stock; store at −20°C in single-use aliquots.
• Set up an enzyme reaction containing substrate (e.g., cortisone or suitable probe for 11β-HSD1 studies), cofactors, buffer at pH 7.4, and serial dilutions of compound maintaining constant DMSO (≤1%).
• Incubate at 25–37°C for 10–60 min; quench and analyze product formation by LC–MS or spectroscopic readout.

Cell-based assay (general outline):

• Dilute DMSO stocks into cell culture media to achieve the desired final concentration with ≤0.1–0.5% DMSO. Pre-test solubility to avoid precipitation.
• Include viability controls and vehicle controls; maintain consistent exposure times.

Data quality:

• Run in technical triplicates and biological replicates. Use curve-fitting with appropriate models and include confidence intervals.

Note: These are generic protocols and are not specific recommendations for BI 187004. Consult the CoA and literature for CAS 1303515-32-3 before executing experiments.

Biological Roles

Item-specific biological targets or roles are not provided in this listing.

General/literature context for this chemotype (non-clinical, research-only):

• Compounds designated as BI 187004 have been discussed in the literature as chemical tools probing the enzyme 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1), which catalyzes the conversion of cortisone to cortisol inside cells, thereby modulating intracellular glucocorticoid tone. Such molecules are used to interrogate steroid metabolism pathways, NADPH-dependent oxidoreductase mechanisms, and metabolic flux in hepatocytes, adipocytes, and other relevant cell types.
• In research settings, these small molecules can help delineate on-target versus off-target effects by comparing biochemical enzyme inhibition with cellular readouts of steroid interconversion.

Important boundaries:

• No medical or therapeutic claims are made for this product. Any mention of biological roles is purely for mechanistic, laboratory research context. Consult primary literature for CAS 1303515-32-3 to align experimental design with known properties of the specific compound batch you are using.

Good practices:

• Verify target engagement using orthogonal assays (e.g., LC–MS quantification of cortisone/cortisol in cell supernatants) alongside biochemical inhibition data.
• Control for cytotoxicity and nonspecific effects by titrating the compound and maintaining consistent vehicle concentrations across conditions.

Buffer Applications

This product is not a buffering agent. Buffer formulation guidance below is provided only insofar as it relates to preparing assay media for small-molecule testing.

• Common assay buffers: HEPES or phosphate-buffered saline (PBS) at pH 7.2–7.6 are frequently used for enzyme and cell-based assays. Include BSA or mild nonionic surfactant (e.g., 0.01–0.05% Tween-20 or Pluronic F-68) if adsorption or precipitation is observed.
• Solvent compatibility: Maintain final DMSO at ≤0.5–1% v/v for most biochemical assays and ≤0.1–0.5% v/v for sensitive cells unless validated otherwise.
• pH considerations: If the compound has ionizable groups (verify structure), assay pH can influence solubility and target interaction; keep pH tightly controlled and constant across conditions.
• Filtration: Use 0.22 µm low-binding filters to clarify assay buffers; do not filter DMSO-rich solutions through cellulose-based membranes.

Not applicable aspects:

• Classic buffer capacity, pKa, and ionic strength specifications are not relevant to the compound itself and thus are not provided in this listing.

Green Alternatives

As a research small molecule standard rather than a bulk solvent or reagent, "green alternative" considerations focus on how you formulate and handle solutions rather than substituting the compound itself.

Greener handling strategies (general):

• Solvent choice: Prefer DMSO or ethanol over chlorinated solvents for stock preparation when compatible with your assay. Use the minimum effective organic cosolvent in aqueous buffers.
• Waste minimization: Prepare small aliquots to reduce expired stock disposal. Use micro-scale assays and 96/384-well formats to limit compound and solvent usage.
• Energy and storage: Store at −20°C as specified, but avoid unnecessary deep-cold shipping by coordinating deliveries to reduce re-icing events. Combine shipments when possible.
• Safer diluents: Employ phosphate- or HEPES-buffered saline with mild surfactant instead of high percentages of organic solvent.

Comparison (general considerations):

• DMSO vs DMF: DMSO is generally preferred from an environmental, health, and assay-compatibility standpoint, though it can enhance dermal absorption—use appropriate PPE.
• Ethanol vs isopropanol: Both are relatively safer and renewable-based; select based on assay tolerance and solubility limits.

Documentation: Record solvent composition and volumes to support accurate green metrics (E-factor, PMI) for your screening campaigns. While the active structure cannot be “greened,” the surrounding workflow can be optimized for safety and sustainability.

Pharmaceutical Uses

No pharmacopeial grade, excipient role, or formulation status is provided for this product. It is supplied strictly for laboratory research use.

General considerations for small-molecule tool compounds (non-clinical):

• Preformulation for in vitro research: When necessary, prepare DMSO stocks and dilute into media with careful control of solvent percentage. For permeability or transport studies, document solvent composition and verify absence of precipitation.
• Stability information: Absent in this listing; consult CoA/SDS and verify by LC–MS after storage. Protect from moisture and light if the chemotype warrants it.

Important limitations:

• No claims are made regarding suitability for human or veterinary use, GMP status, or compliance with USP/EP/JP monographs. Do not use for diagnostic or therapeutic purposes.

Documentation:

• For any translational research steps, obtain full structural and analytical characterization from the CoA and primary literature for CAS 1303515-32-3 to ensure batch-to-batch comparability and to define the free base/acid or salt form if applicable.

Physical Properties

Item-specific specifications:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (MP): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point (BP): Not typically applicable for complex small-molecule solids; Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable for solids; Not specified for this item; refer to CoA/Spec Sheet.
• Water content, metal limits, residual solvents, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance for this chemotype (non-spec):

• Physical state: Many 11β-HSD1 inhibitor chemotypes are off-white to light-colored crystalline solids with limited aqueous solubility.
• Solubility profile: Commonly soluble in polar aprotic organic solvents (DMSO, DMF, DMAc) and in certain chlorinated or aromatic solvents. Aqueous solubility often improves with co-solvents (DMSO, ethanol) or pH adjustment if ionizable groups are present.
• logP/logD: These series often possess moderate-to-high lipophilicity to access intracellular enzyme targets; exact values for BI 187004 should be sourced from the CoA or primary literature for CAS 1303515-32-3.

Practical tips (general):

• Prepare concentrated DMSO stock solutions (e.g., 10–50 mM) and dilute into assay buffers with attention to final DMSO content (typically ≤0.5–1% v/v in biochemical assays). Filter sterilize if needed using low-binding membranes.

Quality and Grades

Item-specific details in this listing:

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting grades for small-molecule research reagents (general):

• Research grade typically supports discovery biology/chemistry. Purity is often specified by HPLC area % with supporting NMR/MS identity. Low-level residual solvents and water are controlled within internal specifications.
• HPLC or screening grade emphasizes chromatographic purity and suitability for high-throughput screening (HTS), with attention to identity confirmation, low non-volatile residue, and batch-to-batch consistency.
• If offered as salt vs free base/acid, confirm counter-ion content and assay (wt%) to prepare accurate molar solutions.

What to check on the CoA for BI 187004:

• HPLC purity method and result, identity confirmation (1H NMR, HRMS), assay, and residual solvent profile.
• Water content (Karl Fischer) and form (amorphous vs crystalline) if relevant to solubility and handling.
• Any noted polymorph or solvate form; these can affect dissolution rate and bioassay behavior.

Implications for use:

• For screening or mechanistic enzymology, verify exact purity and form to ensure reproducible potency readouts. Record batch/lot in all data packages for traceability.

Reaction and Applications

Scope for this item is primarily as a characterized small molecule for research screening rather than as a synthetic reagent. No manufacturer application text is provided in this listing.

Research usage context (general):

• BI 187004 has been reported in the literature within the class of small molecules interrogating 11β-HSD1 enzymology. Typical applications include biochemical assays with recombinant enzyme, target engagement experiments, and cell-based readouts where 11β-HSD1 activity is relevant to steroid metabolism. Avoid therapeutic or clinical use; this product is for research only.

Assay setup considerations (general):

• Stock solutions: Prepare in anhydrous DMSO and store in aliquots at −20°C. Protect from light if the scaffold contains photo-labile heteroaromatics (verify via structure/CoA).
• Serial dilution: Use polypropylene plates/tubes and low-bind tips. Maintain consistent DMSO across wells to control for solvent effects.
• Controls: Include vehicle controls, positive/negative controls for enzyme activity, and, if available, orthogonal assay formats (e.g., LC–MS-based steroid conversion) to confirm on-target effects.

Analytical characterization (general):

• Monitor stability by LC–MS and HPLC after storage. Assess potential hydrolysis of amide/urea linkages or oxidative degradation if exposed to air/light.

Note: Specific mechanistic data, kinetic parameters, or cellular potency for BI 187004 are not included in this product data and should be sourced from primary literature for CAS 1303515-32-3.

Reaction Conditions

This product is intended as a research tool compound rather than as a reagent to run chemical reactions. Consequently, item-specific reaction conditions are not applicable.

If you are synthesizing or modifying related heteroaryl small molecules (general literature guidance):

• Cross-coupling: For aryl–heteroaryl unions, Pd-catalyzed Suzuki–Miyaura conditions (e.g., Pd2(dba)3/XPhos, K3PO4, 70–100°C, dioxane/H2O) are common. Buchwald–Hartwig amination may be used for C–N bond formation with appropriate ligands (e.g., BrettPhos, tBuONa, toluene, 80–110°C).
• Amide formation: HATU/DIPEA or EDCI/HOBt (or Oxyma) in DMF/CH2Cl2 at 0–25°C, 1–12 h, with careful control to limit epimerization if chiral centers are present.
• SNAr: Activated heteroaryl chlorides/fluorides can be displaced by amines under mild basic conditions (DIPEA, 20–60°C) in polar aprotic solvents.
• Purification and analysis: Use RP-HPLC with water/acetonitrile + 0.1% formic acid for analytical tracking; verify identity by HRMS and NMR.

These conditions are general literature guidance and are not specifications for BI 187004. Always verify compatibility with the exact functional groups once the structure is confirmed from the CoA or primary references for CAS 1303515-32-3.

Safety and Handling

Item-specific hazard data provided in this listing:

• Signal word: Not specified; refer to SDS.
• H-statements: Not specified; refer to SDS.
• GHS classification and pictograms: Not specified; refer to SDS.

General laboratory safety guidance (non-specific; defer to SDS for authority):

• PPE: Use lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood to avoid inhalation of dust or aerosols.
• Avoid contact with skin and eyes; wash thoroughly after handling.
• Incompatibilities: Avoid strong oxidizers and strong acids/bases unless compatibility is established for your protocol. Do not heat to decomposition.
• First aid (overview): If inhaled, move to fresh air; if on skin, wash with soap and water; if in eyes, rinse cautiously with water for several minutes; if ingested, rinse mouth and seek medical advice. Always follow your institution’s emergency procedures.
• Environmental precautions: Prevent release to the environment; collect spills with inert absorbent and dispose of according to local regulations.
• Special risks for small-molecule research solids: Potential for dust formation; weigh inside containment. For DMSO solutions, remember DMSO facilitates dermal absorption of solutes—avoid skin contact.

Always consult the product’s SDS for definitive hazard classification, exposure limits, transport information, and recommended fire-fighting measures.

Solvent Selection

Item-specific solvent specifications are not provided. The following guidance reflects typical behavior of lipophilic heteroaryl small molecules used in enzyme studies.

• Primary dissolution solvent: DMSO is usually preferred due to broad solvating power and assay compatibility at ≤0.5–1% v/v.
• Alternative solvents: DMF or NMP for stock preparation (if DMSO is unsuitable), with subsequent dilution into aqueous buffers containing surfactants (e.g., 0.01–0.05% Tween-20) to mitigate precipitation. Ethanol or isopropanol can be used as co-solvents in some biochemical assays.
• Aqueous media: Expect limited water solubility; pre-dissolve in anhydrous DMSO before dilution. Consider pH adjustment only if the compound has ionizable groups (verify from CoA/structure).
• Solvent quality: Use anhydrous, low-peroxide solvents to prevent degradation of sensitive motifs. Filter solutions using PTFE or PES membranes.

Quick comparison (general):

• DMSO: Highest solvency; widely compatible with biochemical assays at low percentages.
• DMF/NMP: Strong solvency but less favored in biological assays; verify compatibility and cytotoxicity if using cellular systems.
• Ethanol/IPA: Lower solvency but frequently acceptable at ≤1–2% in cell-based assays.

Practical tips:

• Prepare concentrated master stocks (e.g., 10–50 mM) and aliquot to minimize freeze–thaw. Inspect for precipitation after dilution and gently warm (≤37°C) or sonicate briefly if needed.

Storage and Reconstitution

Item-specific conditions:

• Storage temperature: Store at −20°C (as provided in product data).
• Shipping conditions: Shipped in an ice chest with ice pads (as provided in product data).
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution (general guidance for small-molecule solids):

• Solvent: Use anhydrous DMSO to prepare concentrated stock solutions (e.g., 10–50 mM). If an ionizable form is confirmed, alternative solvents (DMF, ethanol) may be considered based on solubility testing.
• Procedure: Allow vial to equilibrate to room temperature before opening to minimize moisture condensation. Weigh quickly in a low-humidity environment (desiccator or glovebox if necessary). Dissolve with gentle vortexing/sonication.
• Aliquoting: Divide into single-use aliquots in low-bind polypropylene tubes to prevent repeated freeze–thaw and adsorption losses.
• Storage of solutions: Store aliquots at −20°C or below, protected from light. Avoid repeated freeze–thaw cycles; discard aliquots showing precipitation or discoloration.

Stability notes:

• No item-specific stability or sensitivity data are provided. As a precaution, minimize exposure to air, moisture, and light. Verify integrity periodically by HPLC/LC–MS.

Research use note:

• For research use only. Not for human or veterinary use.

Structure and Identity

Brief overview: BI 187004 is a research small molecule. Item-specific identifiers are limited in this listing; consult the CoA/SDS for definitive structural data.

• Product name: BI 187004 (research small molecule)
• CAS: 1303515-32-3 (item-specific)
• PubChem CID: 67223373 (item-specific)
• InChIKey (as provided): 389918 (item-specific; note that typical InChIKeys are 27-character hashes — verify on CoA/SDS)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general/literature context):

• BI 187004 is reported in the literature as a small-molecule inhibitor from the 11β-HSD1 inhibitor chemotype space, which commonly features heteroaromatic cores and amide/urea motifs for enzyme binding. Exact functional group set for this item should be verified from the CoA or primary literature corresponding to CAS 1303515-32-3.

2D structure (descriptive, literature-level):

• Literature sources depict members of this series as polyheteroaryl scaffolds with one or more ring systems connected by amide linkages and containing multiple hydrogen-bond acceptors/donors positioned for active-site engagement. Because the definitive structure string is not specified here, treat any diagrammatic interpretation as provisional pending the official structure file from the CoA or supplier database.

Synthetic Utility

BI 187004 is sold as a finished small molecule for research use and is not primarily intended as a synthetic reagent. Without an item-specific structure string in this listing, route design is speculative. The information below is general to heteroaryl amide/urea small molecules.

General synthetic insights (literature-level):

• Core assembly: Many related scaffolds are built via heteroaryl–aryl coupling (e.g., Suzuki–Miyaura, Buchwald–Hartwig) followed by amide/urea formation using carbamoyl chlorides, CDI, or coupling reagents (HATU, EDCI, PyBOP).
• Late-stage diversification: Installation of solubilizing groups or polar heterocycles is often achieved via N-arylation, SNAr on activated heteroarenes, or nucleophilic acyl substitution.
• Protecting group strategy: Boc/CBz for amines; MOM/benzyl for heteroaryl alcohols if present. Final deprotections should be selected to avoid degrading sensitive heteroaryl motifs.
• Purification: Reverse-phase preparative HPLC is common to achieve >95% area purity; crystallization may be possible depending on salt form.

Analytical controls:

• Confirm structure and purity by 1H/13C NMR, HRMS, and HPLC. Where multiple tautomers are possible in poly-heteroaryl systems, 2D NMR (HSQC/HMBC/NOESY) aids unambiguous assignment.

Note: Specific functional groups, stereochemistry, and named transformations for BI 187004 cannot be detailed here without the definitive structure; refer to the CoA or primary literature for CAS 1303515-32-3.

Target Specificity

Item-specific target details are not provided in this listing.

General literature context (non-validated here):

• Compounds known as BI 187004 have been described in publications assessing selective inhibition of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). However, no target affinity, selectivity panel data, or kinetic mechanism is provided in this product entry.

For rigorous research use:

• Obtain primary references for CAS 1303515-32-3 to confirm biochemical potency, species cross-reactivity, and off-target profiling (e.g., 11β-HSD2 counter-screen, CYP panel, hERG, etc.), as appropriate for your application.
• Report the batch/lot and any experimentally determined IC50/Ki in your methods section; do not rely on informal summaries when target specificity is critical to conclusions.

よくある質問

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 1303515-32-3, the molecular formula is C21H18N4O, and the molecular weight is 342.4 g/mol. InChIKey VVZNCSHIBODHMZ-UZLBHIALSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.