121-40-4 Usage
Uses
Used in Pharmaceutical Industry:
(1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE is used as a therapeutic agent for the treatment of SWI/SNF complex-deficient cancers. It is particularly effective in cancers that comprise the glutathione (GSH) metabolic pathway, as it can inhibit the catalytic activity of BTK, leading to the suppression of tumor growth and progression.
Hazard
Mycotoxin; poison; mutagen.
Biological Activity
Selective inhibitor of Bruton's tyrosine kinase (BTK). Inhibits the interaction between PKCbII and BTK (IC 50 ~ 30 mM) and the catalytic activity of BTK but does not affect the activity of PKC. Has little effect on the activities of Lyn, Syk, PKA, casein kinase I, ERK1, ERK2 and p38 kinases.
Biochem/physiol Actions
Terreic acid (TA) is a covalent inhibitor of the bacterial cell wall biosynthetic enzyme MurA. The survival of most bacteria depends on the functionality of this cytosolic enzyme. The inactivation of MurA requires the presence of UDP-N-acetylglucosamine 1-Carboxyvinyl transferase, which catalyzes the first step in the biosynthesis of the bacterial cell wall. TA is more potent than the known MurA inhibitor Fosphomycin. TA was also found to severely inhibit the transcription of TNFα and IL-2. TA inhibits protein synthesis by blocking the formation of leucyl-tRNA in sensitive bacteria and inhibits the catalytic effect of Bruton′s tyrosine kinase (Btk), an important factor in B-cell and mast cell activation, by inducing conformational changes that prevent Protein Kinase C (PKC) from interacting with the Btk domain. Moreover, recent studies have demonstrated that TA exhibits a very high level of radical scavenging activity.
Purification Methods
Crystallise terreic acid from *C6H6, *C6H6/pet ether or hexane. Sublime it 80-100o/1mm. [Beilstein 17 IV 6698.]
Check Digit Verification of cas no
The CAS Registry Mumber 121-40-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 1 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 121-40:
(5*1)+(4*2)+(3*1)+(2*4)+(1*0)=24
24 % 10 = 4
So 121-40-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1
121-40-4Relevant articles and documents
Synthesis of Hydroxyquinones and Related Compounds: Semisquaric Acids, (+/-)-Terreic Acid, (+/-)-Perezone, and (+/-)-Isoperezone
Enhsen, Alfons,Karabelas, Kostas,Heerding, Julia M.,Moore, Harold W.
, p. 1177 - 1185 (2007/10/02)
tert-Butoxyquinones were prepared from the thermal ring expansion of 4-alkynyl-, 4-alkenyl-, and 4-aryl-tert-butoxycyclobutenones and shown to be readily converted to hydroxyquinones upon treatment with trifluoroacetic acid at low temperature.This is a useful transformation since no reliable general route to hydroxyquinones has previously been available.The synthetic scope of this methodology as well as its specific utilization in the synthesis of a semisquaric acid, and the natural products, (+/-)-terreic acid, (+/-)-perezone, and (+/-)-isoperezone, are described.
