93633-32-0

Basic information

• Product Name: Pentanedioic acid, 2-methylene-, 5-methyl ester
• CAS NO: 93633-32-0
• Molecular Formula: C7H10O4
• Molecular Weight: 158.154
• Mol File: 93633-32-0.mol

Chemical Properties

• CAS DataBase Reference: Pentanedioic acid, 2-methylene-, 5-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanedioic acid, 2-methylene-, 5-methyl ester(93633-32-0)
• EPA Substance Registry System: Pentanedioic acid, 2-methylene-, 5-methyl ester(93633-32-0)

Safety Data

• Hazardous Substances Data: 93633-32-0(Hazardous Substances Data)

Upstream product

• 5621-44-3 dimethyl 2-methylenepentanedioate 

Downstream Products

• 959931-12-5 C₁₉H₂₅NO₄ 
• 959931-13-6 C₁₉H₂₅NO₄ 
• 959931-16-9 C₁₈H₂₂BrNO₃ 
• 959931-17-0 C₁₈H₂₂N₂O₅ 
• 959931-15-8 C₁₈H₂₂FNO₃ 
• 959931-14-7 C₁₉H₂₅NO₄ 
• 1291072-88-2 C₂₀H₂₇NO₄ 
• 1291072-84-8 C₂₀H₂₇NO₃ 
• 1291072-89-3 C₁₉H₂₄FNO₃ 
• 1291072-90-6 C₁₉H₂₄ClNO₃ 
• 1291072-93-9 C₁₉H₂₄ClNO₃ 
• 1291072-99-5 C₁₉H₂₄BrNO₃ 
• 1291073-01-2 C₁₉H₂₄BrNO₃ 
• 1291073-03-4 C₂₀H₂₄F₃NO₃ 

Relevant articles and documents

Lactam-based HDAC inhibitors for anticancer chemotherapy: Restoration of RUNX3 by posttranslational modification and epigenetic control

Expression and stability of the tumor suppressor runt-related transcription factora 3 (RUNX3) are regulated by histone deacetylase (HDAC). HDAC inhibition alters epigenetic and posttranslational stability of RUNX3, leading to tumor suppression. However, HDAC inhibitors can nonselectively alter global gene expression through chromatin remodeling. Thus, lactam-based HDAC inhibitors were screened to identify potent protein stabilizers that maintain RUNX3 stability by acetylation. RUNX activity and HDAC inhibition were determined for 111 lactam-based analogues through a cell-based RUNX activation and HDAC inhibition assay. 3-[1-(4-Bromobenzyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-N- hydroxypropanamide (11-8) significantly increased RUNX3 acetylation and stability with relatively low RUNX3 mRNA expression and HDAC inhibitory activity. This compound showed significant antitumor effects, which were stronger than SAHA, in an MKN28 xenograft model. Thus, we propose a novel strategy, in which HDAC inhibitors serve as antitumor chemotherapeutic agents that selectively target epigenetic regulation and protein stability of RUNX3.

A catalytic approach to the MH-031 lactone: Application to the synthesis of geralcin analogs

A concise, 5-step synthesis of the hepatoprotective lactone MH-031 was achieved. Our approach utilizes several catalytic processes, namely, a Rauhut-Currier reaction, a chemoselective Fisher esterification, and a ring closing metathesis. Further elaboration of this lactone yielded the hydrazide natural product geralcin A and dihydrogeralcin B, a saturated analog of geralcin B. Biological evaluation of the latter indicated that the presence of the enehydrazide moiety in geralcin B is critical for anticancer activity.

Synthesis, enzymatic inhibition, and cancer cell growth inhibition of novel δ-lactam-based histone deacetylase (HDAC) inhibitors

δ-Lactam-based hydroxamic acids, inhibitors of histone deacetylase (HDAC), have been synthesized via ring closure metathesis of key diene intermediates followed by conversion to hydroxamic acid analogues. The hydroxamic acids 12a, 12b, and 17c showed potent inhibitory activity in HDAC enzyme assay. The hydroxamic acid 12b exhibited growth inhibitory activity on five human tumor cell lines, showing good sensitivity on the MDA-MB-231 breast tumor cell.