145013-06-5

Upstream product

• 145013-05-4 tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate 
• 100-46-9 benzylamine 
• 207857-15-6 1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine 
• 322474-21-5 N,N'-bis-Boc-S-methyl-isothiourea 
• 62-53-3 aniline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 216584-22-4 N¹,N²,N³-tris(tert-butoxycarbonyl)guanidine 
• 187022-33-9 4-nitro-1-H-pyrazole-1-carboxamidine 
• 152120-54-2 N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine 
• 332882-82-3 1,3-bis(t-butoxycarbonyl)guanidine 

Downstream Products

• 204447-02-9 [benzylamino-(3-benzylureido)methylene]carbamic acid tert-butyl ester 
• 2211-57-6 N-benzylguanidine 
• 1197-49-5 1-benzylguanidine hydrochloride 

Relevant academic research and scientific papers

Conversion of N,N'-bis(tert-butoxycarbonyl)guanidines to N-(N'-tert-butoxycarbonylamidino)ureas

Surprising aminolysis of bis-Boc-protected guanidines in refluxing THF leads to the corresponding monoBoc substituted amidinoureas.

A new reagent for solid and solution phase synthesis of protected guanidines from amines

A new reagent 4-nitro-1-H-pyrazole-1-[N, N'-bis(tert- butoxycarbonyl)]carboxamidine has been developed to effect the rapid and efficient synthesis of bis(carbamate)-protected guanidines from primary and secondary amines. The reagent is a more electrophili

A novel traceless resin-bound guanidinylating reagent for secondary amines to prepare N,N-disubstituted guanidines

Matrix presented We report the development of a solid support-linked guanidinylating reagent. This reagent consists of a urethane-protected triflyl guanidine attached to the resin via a carbamate linker. It allows for rapid synthesis of guanidines from a variety of amines. It provides access to N-alkyl/aryl-or N,N-dialkylguanidines under mild conditions. Cleavage with 50% TFA produces target molecules in high yields and purity. The ability to guanidinylate secondary amines is a significant feature of this guanidinylating reagent.

Synthesis and biological evaluation of amidinourea derivatives against herpes simplex viruses

Current therapy against herpes simplex viruses (HSV) relies on the use of a few nucleoside antivirals such as acyclovir, famciclovir and valacyclovir. However, the current drugs are ineffective against latent and drug-resistant HSV infections. A series of amidinourea compounds, designed as analogues of the antiviral drug moroxydine, has been synthesized and evaluated as potential non-nucleoside anti-HSV agents. Three compounds showed micromolar activity against HSV-1 and low cytotoxicity, turning to be promising candidates for future optimization. Preliminary mode of action studies revealed that the new compounds act in an early stage of the HSV replication cycle, just after the viral attachment and the entry phase of the infection.

Cooperative Multipoint Recognition of Sialic Acid by Benzoboroxole-Based Receptors Bearing Cationic Hydrogen-Bond Donors

Sialic acid recognition remains an interesting and challenging target in molecular receptor design. Herein, we report a series of benzoboroxole-based receptors in which cationic hydrogen-bond donors have been introduced and shown to promote multipoint sialic acid recognition. One striking feature revealed by these receptors is that the carboxylate sialic acid residue is the primary binding determinant for recognition by benzoboroxole, in which the presence of charge-reinforced hydrogen bonds results in enhanced selectivity for sialic acid over other carbohydrates and a 4.5-fold increase in affinity. These findings open up wide possibilities for benzoboroxole-based receptors use in life science research, biotechnology, and diagnostics.

Iodine-catalyzed guanylation of amines with N, N ′-di-Boc-thiourea

Herein, we report that iodine-catalyzed guanylation of primary amines can be accomplished with N,N′-di-Boc-thiourea and TBHP to afford the corresponding guanidines in 40-99% yields. Oxidation of the HI byproduct by TBHP eliminates the need for an extra base to prevent the protonation of substrates and makes the reaction especially useful for both electronically and sterically deactivated primary anilines.

Synthesis of guanidines via the I2 mediated desulfurization of N,N′-di-Boc-thiourea

The I2 mediated desulfurization of N,N′-di-Boc-thiourea was developed. Various primary amines, including sterically and electronically deactivated primary amines, were transformed into the corresponding bis-Boc protected guanidines under mild conditions.

Synthetic method for preparing substituted guanidine by iodine-catalyzed thiourea desulfurization

The invention discloses a synthetic method for preparing substituted guanidine by iodine-catalyzed thiourea desulfurization, aiming at the fact that excessive heavy metals or oxidizing agents are required for synthesizing substituted guanidine in a traditional method. According to the method, starting from economical N,N'-di-tert-butyloxycarbonyl thiourea easy to obtain, a catalyst-involved thiourea desulfurization reaction is carried out to realize the preparation of guanidine containing different substituents. The synthetic method for preparing the substituted guanidine does not need additional alkali, has high atom economy and is mainly used for late modification of drug molecules and natural products.

Method for synthesizing substituted guanidine

The invention provides a method for synthesizing substituted guanidine. The method of the invention is provided against heavy metals or complex oxidants needed in convectional methods for synthesizingthe substituted guanidine. The method comprises the following steps: carrying out an elemental iodine-mediated thiourea desulphurization reaction on economical and easily available N,N'-bis-tert-butoxycarbonylthiourea to generate an active carbodiimide active intermediate, and attacking the intermediate with free amine to remove a protecting group in order to finally realize the preparation of the guanidine containing different substituent groups. The method for synthesizing substituted guanidine of the present invention has the advantages of mild reaction conditions and high efficiency, andis expected to be applied to later modification of drug molecules and natural products.

Synthesis and Biological Evaluation of Amidinourea and Triazine Congeners as Inhibitors of MDA-MB-231 Human Breast Cancer Cell Proliferation

A series of novel amidinourea derivatives was synthesized, and the compounds were evaluated as inhibitors of MDA-MB-231 human breast cancer cell proliferation. In addition, a second series of triazine derivatives designed as rigid congeners of the amidinoureas was synthesized, and the compounds were evaluated for their antiproliferative activity. Among the two series, amidinourea 3 d (N-[N-[8-[[N-(morpholine-4-carbonyl)carbamimidoyl]amino]octyl]carbamimidoyl]morpholine-4-carboxamide) emerged as a potent anticancer hit compound with an IC50value of 0.76 μm, similar to that of tamoxifen.