50733-91-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromoheptanoylchloride is used as a building block for the synthesis of biologically active molecules, contributing to the development of new pharmaceutical compounds. Its reactivity allows for the creation of diverse drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Bromoheptanoylchloride serves as a key intermediate in the synthesis of agricultural chemicals. Its role in formulating effective pest control agents and other agrochemical products is vital for enhancing crop protection and yield.
Used in Organic Synthesis:
2-Bromoheptanoylchloride is utilized as a reagent in organic synthesis for preparing a variety of compounds. Its ability to react with different nucleophiles makes it a valuable tool in the creation of new chemical entities for research and industrial applications.

Upstream product

• 111-16-0 heptanedioic acid 
• 3710-42-7 7-hydroxyheptanoic acid 
• 29823-18-5 ethyl 7-bromoheptanoate 
• 30515-28-7 7-bromoheptanoic acid 

Downstream Products

• 792935-73-0 7-bromo-heptanoic acid (4-phenyl-thiazol-2-yl)-amide 
• 144970-09-2 N,N'-2,6-pyridinediylbis<7-(3-formyl-2-hydroxyphenoxy)heptanamide> 
• 144970-08-1 N,N'-2,6-pyridinediylbis<7-<3-formyl-2-(2-propenyloxy)phenoxy>heptanamide> 
• 139503-63-2 7-[4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-oxazolyl]heptanenitrile 
• 93645-62-6 4-(7-Bromo-heptanoyloxy)-benzoic acid 4-methoxy-phenyl ester 
• 129090-58-0 7-Bromo-heptanoic acid 2,3,4,5,6-pentakis-(7-bromo-heptanoyloxy)-cyclohexyl ester 
• 129090-54-6 7-Bromo-heptanoic acid pentakis-(7-bromo-heptanoyloxy)-phenyl ester 
• 1239468-24-6 3-{(benzyloxy)[7-(dimethylamino)heptanoyl]amino}propanoic acid tert-butyl ester 
• 1239468-31-5 3-[(benzyloxy)(7-bromoheptanoyl)amino]propanoic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis, binding, and functional properties of tetrahydroisoquinolino-2-alkyl phenones as selective σ2R/TMEM97 ligands

Sigma-2 receptor (σ2R/TMEM97) has been implicated to play important roles in multiple cellular dysfunctions, such as cell neoplastic proliferation, neuro-inflammation, neurodegeneration, etc. Selective σ2 ligands are believed to be promising pharmacological tools to regulate or diagnose various disorders. As an ongoing effort of discovery of new and selective σ2 ligands, we have synthesized a series of tetrahydroisoquinolino-2-alkyl phenone analogs and identified that 10 of them have moderate to potent affinity and selectivity for σ2R/TMEM97. Especially, 4 analogs showed Ki values ranging from 0.38 to 5.1 nM for σ2R/TMEM97 with no or low affinity for sigma-1 receptor (σ1R). Functional assays indicated that these 4 most potent analogs had no effects on intracellular calcium concentration and were classified as putative σ2R/TMEM97 antagonists according to current understanding. The σ2R/TMEM97 has been suggested to play important roles in the central nervous system. Based on published pharmacological and clinical results from several regarded σ2R/TMEM97 antagonists, these analogs may potentially be useful for the treatment of various neurodegenerative diseases.

Illiberis ulmivora Graeser sex attractant and preparation method thereof

The invention provides an Illiberis ulmivora Graeser sex attractant, which comprises cis-7-dodecenoic acid-2-butyl ester and cis-9-tetradecenoic acid-2-butyl ester. The invention also provides a preparation method of the Illiberis ulmivora Graeser sex attractant, which comprises the steps of reducing pimelic acid and azelaic acid into 7-hydroxyheptanoic acid through lithium aluminum hydride, brominating the 7-hydroxyheptanoic acid, performing acylating chlorination on the 7-hydroxyheptanoic acid and thionyl chloride, esterifying the 7-hydroxyheptanoic acid and the thionyl chloride with sec-butyl alcohol to form 7-bromoheptanoic acid-2-butanol ester and 9-bromononanoic acid-2-butanol ester, preparing corresponding phosphine salt from the 7-bromoheptanoic acid-2-butanol ester and the 9-bromononanoic acid-2-butanol ester and triphenylphosphine, and then carrying out wittig reaction with n-valeraldehyde to synthesize a target compound. According to the Illiberis ulmivora Graeser sex attractant and the preparation method thereof, raw materials are easy to obtain, operation is easy and convenient, the cost is low, the product yield is high, the technological process is short, synthesis reaction conditions are mild, no danger exists, the product is easy to separate, for the stereoisomerization problem, unstable phosphorus ylide reacts with fatty aldehyde, the product is mainly cis-olefin, the yield is 90% or above, the stable phosphorus ylide reacts with fatty aldehyde, and the product is mainly trans-olefin.

Discovery of Wogonin-based PROTACs against CDK9 and capable of achieving antitumor activity

Wogonin is a natural product isolated from the Scutellaria baicalensis and has been proved to be a potent and selective inhibitor of CDK9. Using this scaffold, we designed and synthesized a series of proteolysis targeting chimeras (PROTACs) targeting CDK9 by recruiting ubiquitin E3 ligase cereblon (CRBN). For constructing diverse Wogonin-based PROTACs, a “click chemistry” approach was employed for the synthesis of CDK9-targeting PROTACs. The results of western blotting assays showed that compounds containing triazole group in the linker could selectively downregulate the intracellular CDK9 level. Among these compounds, 11c could selectively degrade CDK9 in a concentration-dependent manner. In addition, the application of the proteasome inhibitor MG132 and CRBN siRNA silencing confirmed that 11c could promote the proteasome-dependent and CRBN-dependent degradation. Consistent with the degradation of the CDK9 protein, 11c selectively inhibits proliferation of CDK9-overexpressed cancer cells. Thus, our Wogonin-based PROTAC would be an efficient probe that induces the degradation of CDK9.

Flexible analogues of WAY-267,464: Synthesis and pharmacology at the human oxytocin and vasopressin 1a receptors

A previously identified, non-peptidic oxytocin (OT) receptor agonist WAY-267,464 (1) and nine novel derivatives (3, 4a-7a, 4b-7b) were synthesised and evaluated in vitro with the aim of systematically exploring hydrogen bonding interactions and ligand flexibility. All analogues were subjected to competition radioligand binding assays at human oxytocin (OT) and arginine vasopressin 1a (V1a) receptors. Physiological activity was determined using whole cell IP1 accumulation assays. Under these conditions, WAY-267,464 had higher affinity for the V1a receptor compared to the OT receptor (8.5x more selective) with poor functional selectivity (2x selective for OT receptor agonism over V1a receptor antagonism). Methylation of the resorcinol moiety (3) reversed the OT receptor pharmacological profile, removing agonist activity and inducing antagonist activity, without altering V1a receptor pharmacology. All flexible tethered derivatives removed OT receptor affinity and activity resulting in the generation of highly selective V1a receptor ligands.

Hydroxamic acid derivative and JHDM inhibitor

PROBLEM TO BE SOLVED: To provide a compound capable of selectively inhibiting the function of JHDM, and a JHDM inhibitor. SOLUTION: This hydroxamic acid derivative expressed by formula (1a) [wherein, R1and R2are each independently alkyl which may have a branch; and (n) is an integer of ≥1] or general formula (1b) [wherein, ring X is a 3 to 8-membered saturated carbon ring; and (n) is an integer of ≥1], its pharmaceutically acceptable salt, hydrate, solvate or prodrug is provided. COPYRIGHT: (C)2011,JPOandINPIT

HDAC INHIBITING DERIVATIVES OF CAMPTOTHECIN

The disclosure includes hydroxamic compounds of Formula I: (Formula I) wherein Z, L, R1, R2, and R3 are defined herein. Also disclosed is a method for treating a neoplastic disease or an immune disease with these compounds.

Fluoroalkene modification of mercaptoacetamide-based histone deacetylase inhibitors

Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. The mercaptoacetoamide-based inhibitors are reported to be less toxic than hydroxamate and are worthy of further consideration. Therefore, we have designed a series of analogs as potential inhibitors of HDACs, in which the mercaptoacetamide group was replaced by (mercaptomethyl)fluoroalkene, and their HDAC inhibitory activity was evaluated. Subnanomolar inhibition was observed for all synthetic compounds.

Design, synthesis, enzyme-inhibitory activity, and effect on human cancer cells of a novel series of jumonji domain-containing protein 2 histone demethylase inhibitors

Selective inhibitors of Jumonji domain-containing protein (JMJD) histone demethylases are candidate anticancer agents as well as potential tools for elucidating the biological functions of JMJDs. On the basis of the crystal structure of JMJD2A and a homology model of JMJD2C, we designed and prepared a series of hydroxamate analogues bearing a tertiary amine. Enzyme assays using JMJD2C, JMJD2A, and prolyl hydroxylases revealed that hydroxamate analogue 8 is a potent and selective JMJD2 inhibitor, showing 500-fold greater JMJD2C-inhibitory activity and more than 9100-fold greater JMJD2C-selectivity compared with the lead compound N-oxalylglycine 2. Compounds 17 and 18, prodrugs of compound 8, each showed synergistic growth inhibition of cancer cells in combination with an inhibitor of lysine-specific demethylase 1 (LSD1). These findings suggest that combination treatment with JMJD2 inhibitors and LSD1 inhibitors may represent a novel strategy for anticancer chemotherapy.

Searching for new NO-donor aspirin-like molecules: A new class of nitrooxy-acyl derivatives of salicylic acid

A new class of products in which the phenol group of salicylic acid is linked to alkanoyl moieties bearing nitrooxy functions has been synthesized and studied for their polyvalent actions. The products were stable in acid and neutral media, while they were hydrolyzed in human serum. Their half-lives were dependent upon the structure of alkanoyl moieties. The products showed anti-inflammatory activities similar to aspirin when tested in the carrageenan-induced paw edema assay in the rat. Interestingly, unlike aspirin, they showed reduced or no gastrotoxicity in a lesion model in rats at equimolar doses. A number of them were able to inhibit platelet aggregation induced by collagen in human platelet-rich plasma. All of the products were capable of relaxing rat aortic strips precontracted with phenylephrine in a concentration-dependent manner. Selected members of this new class of nonsteroidal anti-inflammatory drugs might represent possible safer alternatives to aspirin in different clinical settings.

Novel inhibitors of human histone deacetylases: Design, synthesis, enzyme inhibition, and cancer cell growth inhibition of SAHA-based non-hydroxamates

To find novel non-hydroxamate histone deacetylase (HDAC) inhibitors, a series of compounds modeled after suberoylanilide hydroxamic acid (SAHA) was designed and synthesized. In this series, compound 7, in which the hydroxamic acid of SAHA is replaced by a thiol, was found to be as potent as SAHA, and optimization of this series led to the identification of HDAC inhibitors more potent than SAHA. In cancer cell growth inhibition assay, S-isobutyryl derivative 51 showed strong activity, and its potency was comparable to that of SAHA. The cancer cell growth inhibitory activity was verified to be the result of histone hyperacetylation and subsequent induction of p21WAF1/CIP1 by Western blot analysis. Kinetical enzyme assay and molecular modeling suggest the thiol formed by enzymatic hydrolysis within the cell interacts with the zinc ion in the active site of HDACs.