332099-09-9

Basic information

• Product Name: 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid
• CAS NO: 332099-09-9
• Molecular Weight: 246.084
• Mol File: 332099-09-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid(332099-09-9)
• EPA Substance Registry System: 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid(332099-09-9)

Safety Data

• Hazardous Substances Data: 332099-09-9(Hazardous Substances Data)

Upstream product

• 238749-50-3 ethyl 2-bromothieno<3,2-b>pyrrole-5-carboxylate 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 

Relevant articles and documents

RESIN COMPOSITION AND MOLDED ARTICLE

The invention contains a resin and a near infrared fluorescent material which is one type or two or more types of compounds selected from General Formulas (I1) to (I4) and has a maximum fluorescence wavelength of 650 nm or longer. In Formulas, Ra and Rb, Rc and Rd, Rh and Ri, and Rj and Rk form rings together with the nitrogen atom to which Ra, Rc, Rh, and Rj are bonded; Re and Rf represent a halogen atom or an oxygen atom; each of Rl, Rm, Rn, and Ro independently represents a halogen atom, a C1-20 alkyl group, a C1-20 alkoxy group, an aryl group, or a heteroaryl group; Rg, Rr, and Rs represent a hydrogen atom or an electron withdrawing group; and each of Rp and Rq independently represents a hydrogen atom, a halogen atom, a C1-20 alkyl group, a C1-20 alkoxy group, an aryl group, or a heteroaryl group.

Dual functioning thieno-pyrrole fused BODIPY dyes for NIR optical imaging and photodynamic therapy: Singlet oxygen generation without heavy halogen atom assistance

We discovered a rare phenomenon wherein a thieno-pyrrole fused BODIPY dye (SBDPiR690) generates singlet oxygen without heavy halogen atom substituents. SBDPiR690 generates both singlet oxygen and fluorescence. To our knowledge, this is the first example of such a finding. To establish a structure-photophysical property relationship, we prepared SBDPiR analogs with electron-withdrawing groups at the para-position of the phenyl groups. The electron-withdrawing groups increased the HOMO-LUMO energy gap and singlet oxygen generation. Among the analogs, SBDPiR688, a CF3 analog, had an excellent dual functionality of brightness (82290-m-1-cm-1) and phototoxic power (99170-m-1-cm-1) comparable to those of Pc 4, due to a high extinction coefficient (211-000-m-1-cm-1) and balanced decay (Φflu=0.39 and ΦΔ=0.47). The dual functionality of the lead compound SBDPiR690 was successfully applied to preclinical optical imaging and for PDT to effectively control a subcutaneous tumor. Being in a relationship: We discovered and identified key structure-photophysical property relationships within BODIPY dyes that produce singlet oxygen without heavy halogen atom assistance. The exclusion of heavy atoms increases their brightness, which we successfully translated in vivo. We also demonstrate the phototoxic power through optical-guided photodynamic therapy.

Synthesis and CHK1 inhibitory potency of Hymenialdisine analogues

A series of thieno[3,2-b]pyrroloazepinones derivatives related to Hymenialdisine were prepared and tested for CHK1 inhibitory activity. Nanomolar inhibitions were achieved when electron-withdrawing substituents were introduced at position 3 of the thiophene ring.