163391-76-2

Basic information

• Product Name: STACHYBOTRYLACTAM
• Synonyms: STACHYBOTRYLACTAM;2-deoxy F1839A
• CAS NO: 163391-76-2
• Molecular Formula: C24H33NO3
• Molecular Weight: 383.529
• Mol File: 163391-76-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 210℃ (Decomposition) (ethyl acetate )
• Boiling Point: 630.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.28±0.1 g/cm3(Predicted)
• Storage Temp.: ?20°C
• PKA: 9.39±0.70(Predicted)
• CAS DataBase Reference: STACHYBOTRYLACTAM(CAS DataBase Reference)
• NIST Chemistry Reference: STACHYBOTRYLACTAM(163391-76-2)
• EPA Substance Registry System: STACHYBOTRYLACTAM(163391-76-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 163391-76-2(Hazardous Substances Data)

Usage

Description

Stachybotrylactam is an unusual spirodihydrobenzofuranlactam mycotoxin derived from the Stachybotrys sp. It exhibits immunosuppressant properties and weak HIV protease activity. STACHYBOTRYLACTAM belongs to a structural class that demonstrates a range of activities, such as antiviral, endothelin, and pancreatic cholesterase inhibition.

Uses

Used in Pharmaceutical Industry:
Stachybotrylactam is used as an immunosuppressant for its ability to suppress the immune system, which can be beneficial in certain medical treatments where the immune response needs to be controlled or reduced.
Additionally, Stachybotrylactam is used as an inhibitor of HIV protease, which plays a crucial role in the replication of the HIV virus. By inhibiting this enzyme, the compound can help in the development of antiretroviral therapies.
Used in Antiviral Applications:
Stachybotrylactam is used as an antiviral agent due to its ability to inhibit the replication of various viruses, making it a potential candidate for the development of new antiviral drugs.
Used in Endothelin Inhibition:
Stachybotrylactam is used as an endothelin inhibitor, which can be beneficial in treating conditions related to endothelin overactivity, such as hypertension and certain cardiovascular diseases.
Used in Pancreatic Cholesterase Inhibition:
Stachybotrylactam is used as an inhibitor of pancreatic cholesterase, an enzyme involved in the breakdown of cholesterol. This inhibition can be useful in the development of treatments for hypercholesterolemia and other cholesterol-related conditions.

Upstream product

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Relevant articles and documents

Chartarolides A-C, novel meroterpenoids with antitumor activities

Three phenylspirodrimane-based meroterpenoids with novel scaffolds, namely chartarolides A-C (1–3), were isolated from a sponge (Niphates recondite) associated fungus Stachybotrys chartarum WGC-25C-6. Their structures were determined on the basis of comprehensive analyses of the spectroscopic data (IR, 1D and 2D NMR, HRESIMS), including the TDDFT-ECD calculation for the assignments of absolute configurations. The biogenetic generation of 1–3 through the conjunction of phenylspirodrimane and mollicellin-type analogues as the precursors was postulated. Chartarolides A-C exhibited significant cytotoxic activities against a panel of human tumor cell lines, and showed strong inhibitory activities against the human tumor related protein kinases of FGFR3, IGF1R, PDGFRb, and TrKB.

Total synthesis and structure revision of Stachybotrys spirolactams

The spirolactam structure 1 reported in 1996 by Roggo et al. has been enantioselectively synthesized in 20 steps from (+)-Wieland-Miescher ketone. Spectra of this synthetic lactam differed from those of the natural spirolactam from the Roggo group, leading to the hypothesis that the natural lactam may be the regioisomer 27, a structure previously ascribed by Jarvis et al. to the natural product stachybotrylactam. This hypothesis was confirmed by the first total synthesis of (-)-stachybotrylactam (27). Double reductive amination of two molecules of aldehyde 29 with one molecule of L-lysine led by analogous chemistry to the first synthesis of the pseudosymmetric "dimer" 30, whose spectra corresponded to those of the natural "dimer" originally assigned structure 5 by the Roggo group.