Cas no 19171-18-7 (4-Nitrothalidomide)

4-Nitrothalidomide is a nitro-substituted derivative of thalidomide, primarily investigated for its potential pharmacological properties. This compound retains the core phthalimide structure of thalidomide but incorporates a nitro group at the 4-position, which may influence its biological activity and stability. Research suggests that 4-Nitrothalidomide could exhibit enhanced reactivity or altered binding affinity compared to its parent molecule, making it a candidate for further study in medicinal chemistry. Its synthetic accessibility and structural modifications offer opportunities for exploring structure-activity relationships in drug development. The compound is typically handled under controlled conditions due to its reactive nitro group, requiring standard safety precautions in laboratory use.
4-Nitrothalidomide structure
4-Nitrothalidomide structure
Product Name:4-Nitrothalidomide
CAS No:19171-18-7
MF:C13H9N3O6
MW:303.227062940598
MDL:MFCD01748356
CID:855431
PubChem ID:134775
Update Time:2025-06-27

4-Nitrothalidomide Chemical and Physical Properties

Names and Identifiers

    • 2-(2,6-Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
    • 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindole-1,3-dione
    • 4-nitro-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
    • 1H-isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-4-nitro-
    • N-(2,6-Dioxo-3-piperidyl)-3-nitrophthalimide
    • 4-Nitrothalidomide
    • Pomalidomide Impurity E
    • Pomalidomide Impurity 11
    • Pomalidomide Intermediates
    • 3-Nitrothalidomide
    • Phthalimide, N-(2,6-dioxo-3-piperidyl)-3-nitro-
    • 3-(1',3'-Dioxo-4'-nitroisoindolinyl-2')-2,6-dioxopiperidine
    • Nitrothalidomide
    • C13H9N3O6
    • KVRCAGKHAZRSQX-UHFFFAOYSA-N
    • BCP10969
    • 3088AH
    • AK1
    • 2-(2,6-dioxopiperidin-3-yl)-4-nitro-1H-isoindole-1,3(2H)-dione
    • AKOS022171482
    • SB66228
    • NS00123006
    • 1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-4-nitro-isoindole
    • DTXSID00940816
    • CS-M1140
    • 4-NITROTHALIDOMIDE, (+/-)-
    • O10454
    • 2-(2,6-DIOXOPIPERIDIN-3-YL)-4-NITRO-ISOINDOLE-1,3-DIONE
    • 2-(2,6Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
    • MFCD01748356
    • UNII-OH13HKS17A
    • 2-(6-Hydroxy-2-oxo-2,3,4,5-tetrahydropyridin-3-yl)-4-nitro-1H-isoindole-1,3(2H)-dione
    • DS-5838
    • 2-(2,6-Dioxo-3-piperidinyl)-4-nitro-1H-isoindole-1,3(2H)-dione
    • 19171-18-7
    • OH13HKS17A
    • SCHEMBL1398974
    • 2-(2,6-dioxopiperidin-3-yl)-4-nitro-2,3-dihydro-1H-isoindole-1,3-dione
    • 2-(2,6-Dioxo-3-piperidinyl)-4-nitro-1H-isoindole-1,3(2H)-dione; 2-(2,6-Dioxopiperidin-3-yl)-4-nitro-isoindole-1,3-dione; 4-Nitro-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione;
    • BDBM50516600
    • EN300-6732712
    • DA-39041
    • Q27894262
    • 2-(2,6-Dioxo-3-piperidyl)-4-nitroisoindoline-1,3-dione
    • SY111881
    • CHEMBL370441
    • MDL： MFCD01748356
    • Inchi： 1S/C13H9N3O6/c17-9-5-4-8(11(18)14-9)15-12(19)6-2-1-3-7(16(21)22)10(6)13(15)20/h1-3,8H,4-5H2,(H,14,17,18)
    • InChI Key： KVRCAGKHAZRSQX-UHFFFAOYSA-N
    • SMILES： O=C1C(CCC(N1)=O)N1C(C2C=CC=C(C=2C1=O)[N+](=O)[O-])=O

Computed Properties

  • Exact Mass: 303.04917
  • Monoisotopic Mass: 303.049
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 1
  • Complexity: 583
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.2
  • Topological Polar Surface Area: 129

Experimental Properties

  • Density: 1.651±0.06 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 603.4°C at 760 mmHg
  • Flash Point: 318.7°C
  • Refractive Index: 1.674
  • Solubility: Very slightly soluble (0.49 g/l) (25 o C),
  • PSA: 126.69

4-Nitrothalidomide Security Information

4-Nitrothalidomide Pricemore >>

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4-Nitrothalidomide Suppliers

Tiancheng Chemical (Jiangsu) Co., Ltd
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(CAS:19171-18-7)2-(2,6-Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
Order Number:LE18138
Stock Status:in Stock
Quantity:25KG,200KG,1000KG
Purity:99%
Pricing Information Last Updated:Friday, 20 June 2025 12:17
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4-Nitrothalidomide Related Literature

Additional information on 4-Nitrothalidomide

Professional Introduction to 4-Nitrothalidomide (CAS No. 19171-18-7)

4-Nitrothalidomide, with the chemical formula C18H12N2O4, is a derivative of thalidomide characterized by the introduction of a nitro group at the 4-position of the tetrahydroisoquinoline core. This compound, identified by its CAS number 19171-18-7, has garnered significant attention in the field of pharmaceutical chemistry and medicinal research due to its unique structural and pharmacological properties. The nitro group not only modifies the electronic and steric environment of the molecule but also opens up possibilities for diverse biological activities, making it a subject of extensive investigation.

The structural motif of 4-Nitrothalidomide shares similarities with thalidomide, a well-known compound historically used for treating morning sickness but later associated with severe teratogenic effects. However, the introduction of a nitro group introduces new pharmacological profiles that may mitigate some of the adverse effects observed with thalidomide while retaining or enhancing certain therapeutic benefits. The nitro group can participate in hydrogen bonding, influence metabolic pathways, and alter receptor binding affinities, all of which are critical factors in drug design and development.

In recent years, 4-Nitrothalidomide has been studied for its potential applications in various therapeutic areas. One of the most promising areas is its role as an anti-inflammatory agent. The nitro group in 4-Nitrothalidomide can undergo reduction to form an amine, which may contribute to its ability to modulate inflammatory pathways. Preclinical studies have suggested that this compound may inhibit the production of pro-inflammatory cytokines such as tumor necrosis factor-alpha (TNF-α) and interleukin-6 (IL-6), making it a candidate for treating chronic inflammatory diseases like rheumatoid arthritis and inflammatory bowel disease.

Furthermore, 4-Nitrothalidomide has shown potential in oncology research. The compound's ability to interfere with microtubule dynamics and cell cycle progression has been explored in several cancer models. Initial studies indicate that 4-Nitrothalidomide may exhibit cytotoxic effects on various cancer cell lines, including breast, ovarian, and colorectal cancers. The exact mechanism by which it exerts these effects is still under investigation, but it is believed that the nitro group may enhance its ability to interact with cellular targets involved in tumor growth and survival.

The pharmacokinetic profile of 4-Nitrothalidomide is another area of interest. Unlike thalidomide, which has a relatively short half-life, studies suggest that 4-Nitrothalidomide may have a longer duration of action due to modifications introduced by the nitro group. This could potentially reduce the frequency of dosing required for therapeutic efficacy. Additionally, the compound's solubility and bioavailability have been optimized through structural modifications, improving its pharmacokinetic properties for clinical use.

In vitro and in vivo studies have also highlighted the potential role of 4-Nitrothalidomide in neurodegenerative diseases. The compound's ability to cross the blood-brain barrier and interact with central nervous system receptors has been investigated in models of Alzheimer's disease and Parkinson's disease. Early research suggests that 4-Nitrothalidomide may protect against neuronal damage by modulating oxidative stress and inflammation within brain tissues. These findings open up new avenues for treating neurodegenerative disorders using this novel derivative.

The synthesis of 4-Nitrothalidomide presents unique challenges due to the sensitive nature of the nitro group and its reactivity under various conditions. Advanced synthetic methodologies have been employed to ensure high yield and purity while minimizing side reactions. Techniques such as nitration followed by reduction or direct functionalization at the 4-position have been explored. These synthetic approaches not only facilitate the production of 4-Nitrothalidomide but also provide insights into optimizing its structure for improved pharmacological activity.

Ethical considerations are paramount when studying compounds derived from thalidomide analogs like 4-Nitrothalidomide. Given the historical context of thalidomide-related teratogenicity, rigorous safety evaluations are conducted before advancing into clinical trials. Preclinical toxicology studies assess developmental toxicity, reproductive toxicity, and long-term health effects to ensure that any potential benefits outweigh risks associated with exposure.

The future direction of research on 4-Nitrothalidomide includes exploring its potential as a lead compound for drug development pipelines targeting inflammation, cancer, and neurodegenerative diseases. Collaborative efforts between academic institutions and pharmaceutical companies are essential to translate preclinical findings into clinical applications. Additionally, computational modeling and high-throughput screening techniques can accelerate the identification of novel derivatives with enhanced therapeutic profiles.

In conclusion,4-Nitrothalidomide (CAS No., 19171-18-7) represents a promising candidate in pharmaceutical research due to its unique structural features and diverse biological activities. Its potential applications in treating chronic inflammatory diseases, cancer, and neurodegenerative disorders make it a valuable compound for further investigation. As research progresses，the full therapeutic spectrum of this derivative will continue to unfold，offering hope for innovative treatments across multiple medical disciplines.

19171-18-7 (4-Nitrothalidomide) Related Products

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Tiancheng Chemical (Jiangsu) Co., Ltd
(CAS:19171-18-7)2-(2,6-Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
LE18138
Purity:99%
Quantity:25KG,200KG,1000KG
Price ($):Inquiry
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