1620-00-4

Usage

Classification

Phytohormone
Found in plants and plays a critical role in growth and development

Function

Natural auxin
Regulates cell division and elongation, root and shoot formation

Physiological processes influenced

Nutrient uptake, fruit development, stress response

Agricultural applications

Promoting root growth in cuttings, enhancing fruit production

Importance

Significant implications for plant biology and agriculture

Upstream product

• 28002-99-5 1-(ethoxycarbonyl)methyleneindane 
• 4709-56-2 ethyl 2-(1H-inden-3-yl)acetate 
• 5796-52-1 inden-1-yliden-acetic acid 
• 480-90-0 1H-inden-1-one 
• 105-36-2 ethyl bromoacetate 
• 83-33-0 inden-1-one 
• 1620-02-6 1-Ethoxycarbonylmethyl-1-hydroxy-indan 

Downstream Products

• 38425-66-0 2-(indan-1-yl)ethanol 
• 7235-16-7 2,3,4,9-tetrahydro-1H-fluoren-1-one 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of novel sulindac derivatives as partial agonists of PPARγ with potential anti-diabetic efficacy

Peroxisome proliferator-activated receptor gamma (PPARγ) is a valuable drug target for diabetic treatment and ligands of PPARγ have shown potent anti-diabetic efficacy. However, to overcome the severe side effects of current PPARγ-targeted drugs, novel PPARγ ligands need to be developed. Sulindac, an identified ligand of PPARγ, is widely used in clinic as a non-steroidal anti-inflammatory drug. To explore its potential application for diabetes, we designed and synthesized a series of sulindac derivatives to investigate their structure-activity relationship as PPARγ ligand and potential anti-diabetic effect. We found that meta-substitution in sulindac's benzylidene moiety was beneficial to PPARγ binding and transactivation. Z rather than E configuration of the benzylidene double bond endowed derivatives with the selectivity of PPARγ activation. The indene fluorine is essential for binding and regulating PPARγ. Compared with rosiglitazone, compound 6b with benzyloxyl meta-substitution and Z benzylidene double bond weakly induced adipogenesis and PPARγ-targeted gene expression. However, 6b potently improved glucose tolerance in a diabetic mice model. Unlike rosiglitazone, 6b was devoid of apparent toxicity to osteoblastic formation. Thus, we provided some useful guidelines for PPARγ-based optimization of sulindac and an anti-diabetic lead compound with less side effects.

Design and synthesis of conformationally constrained analogues of cis-cinnamic acid and evaluation of their plant growth inhibitory activity

1-O-cis-Cinnamoyl-β-d-glucopyranose is known to be one of the most potent allelochemical candidates and was isolated from Spiraea thunbergii Sieb by Hiradate et al. (2004), who suggested that it derived its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. In this study, key structural features and substituent effects of cis-cinnamic acid (cis-CA) on lettuce root growth inhibition was investigated. These structure-activity relationship studies indicated the importance of the spatial relationship of the aromatic ring and carboxylic acid moieties. In this context, conformationally constrained cis-CA analogues, in which the aromatic ring and cis-olefin were connected by a carbon bridge, were designed, synthesized, and evaluated as plant growth inhibitors. The results of the present study demonstrated that the inhibitory activities of the five-membered and six-membered bridged compounds were enhanced, up to 0.27 μM, and were ten times higher than cis-CA, while the potency of the other compounds was reduced.

Substituted methoxy benzylidene indenyl-acetic and propionic acids for treating patients with precancerous lesions

Substituted methoxy benzylidene indenyl compounds are useful in the treatment of precancerous lesions and neoplasms.