2-溴-3-(1H-吲哚-3)-N-甲基马来酰亚胺的合成

以琥珀酰亚胺为起始原料,经过溴化、甲基化后再与吲哚溴化镁加成反应合成了2-溴-3-(1H-吲哚-3)-N-甲基马来酰亚胺,总收率44.8%,其结构经1H NMR和IR确证.     

“一锅串联法”合成2-[(E)-2-2-氯-1-甲基-3-吲哚基)乙烯基]喹啉-3-羧酸(英文)

设计了以2-(溴甲基)喹啉-3-甲酸乙酯(4)与2-氯-1-甲基-3-吲哚醛(5)为起始化合物,通过简便有效的"一锅法"反应,首次将吲哚环引入2-苯乙烯基喹啉骨架模型,从而得到一新颖结构的双杂环化合物,即(E)-2-(2-(2-氯-1-甲基-1H-3-吲哚基)乙烯基)喹啉-3-羧酸(3),其结构通过波谱数据和元素分析得以证实。     

在微波作用、无催化剂的条件下合成3-芳基亚甲基-1，3-二氢-2H-吲哚-2-酮类化合物

用DMF作溶剂，无催化剂、微波辐射的条件下，使吲哚-2-酮(1)和醛、酮(2)发 生缩合反应，合成了3-芳基亚甲基-1，3-二氢-2H-吲哚-2-酮类化合物，时间短、 收率高。     

钯催化2-炔基芳基叠氮与丙烯酸衍生物反应合成1H-吲哚-3-丙烯酸酯（英文）

报道了一种钯催化2-炔基芳基叠氮化合物与丙烯酸衍生物合成吲哚-3-丙烯酸酯的新方法.该方法实现了在温和的反应条件下合成多种1H-吲哚-3-丙烯酸酯衍生物.     

新型2-甲基吲哚衍生物的合成

2-甲基吲哚在草酰氯的存在下与DMF或DMA通过Vilsmeier-Haack反应制得2-甲基-3-甲酰基吲哚(1)或2-甲基-3-乙酰基吲哚(2);1或2与烷基化试剂通过N-烷基化反应合成了一系列新型的2-甲基吲哚类衍生物,其结构经1HNMR,13C NMR,IR和MS表征。     

利用磷试剂制备2-[4,5-二氢化-4-甲基-4-异丙基-5-氧代-1H-咪唑啉-2-基]-苯甲酸的衍生物

本文报告了利用磷试剂制备2-氧代-3-甲基-3-异丙基-3H-咪唑并[2,1-a]-1-氧代-异吲哚及其异构体3-氧代-2-甲基-2-异丙基-2H-咪唑并[2,1-a]-1-氧代-异吲哚和2-[4,5-二氢化-4-甲基-4-异丙基-5-氧代-1H-咪唑啉-2-基]-N,N-二烷基-苯甲酰胺的新方法。本文方法具有反应条件温和、反应时间较短和收率较高等特点。     

1-(2-氨基-3,5-二氰基-4-芳基-4H-吡喃-6-基)愈创兰烃薁的合成

在醋酸铵作用下,通过1-氰乙酰基愈创兰烃薁、芳香醛、丙二腈的三组分反应,一锅法合成了一系列1-(2-氨基-3,5-二氰基-4-芳基-4H-吡喃-6-基)愈创兰烃薁衍生物.该反应操作简单、条件温和、收率良好.产物结构经NMR,MS,IR及元素分析等得以证实.     

2-吗啉基-1-丙基-1H-吲哚-3-取代酰腙类化合物的合成及抑菌活性

以2-吲哚酮为先导化合物,设计合成一系列2-吗啉基-1-丙基-1H-吲哚-3-取代酰腙类化合物.目标化合物结构经核磁共振波谱(1H NMR和13C NMR)和高分辨质谱仪(HRMS)进行确证.采用浊度法测试了目标化合物的离体抑菌活性,抑菌活性测试结果表明:目标化合物对柑橘溃疡病菌(Xanthomonas axonopodis pv.Citri,X.citri)、烟草青枯病菌(Ralstonia.Solanacearum,R.solanacearum)和水稻白叶枯病菌(Xanthomonas oryzae pv.Oryzae,X.oryzae)均表现出一定的抑制活性.化合物2-氰基-N'-((2-吗啉基-1-丙基-1H-吲哚-3-基)亚甲基)乙酰肼(12a)、4-氯-N'-((2-吗啉基-1-丙基-1H-吲哚-3-基)亚甲基)苯甲酰肼(12c)、4-氟-N'-((2-吗啉基-1-丙基-1H-吲哚-3-基)亚甲基)苯甲酰肼(12f)、N'-((2-吗啉基-1-丙基-1H-吲哚-3-基)亚甲基)-4-硝基苯甲酰肼(12k)和N'-((2-吗啉基-1-丙基-1H-吲哚-3-基)亚甲基)异烟肼(12m)表现出较好的抑制活性;化合物12a、12c、12f、12k和12m对水稻白叶枯病菌的EC50为73.79、61.94、59.70、36.72和82.79μg/m L,抑制活性优于对照药叶枯唑和噻菌铜(EC50分别为92.4、120.22μg/m L).     

(S)-2,2,2-三氟-1-(2-甲基-1H-1-吲哚基)乙胺的不对称合成

以2-甲基吲哚为原料,在碱性条件下与α-三氟甲基醛亚胺经加成反应合成了关键中间体——含三氟甲基的(S)-叔丁基亚磺酰胺(3),收率95%,d/r99/1;3脱除保护基得(S)-2,2,2-三氟-1-(2-甲基-1H-1-吲哚基)乙胺(4),收率97%,其结构经1H NMR,13C NMR,19F NMR,FT-IR,EI-MS和HR-EI-MS确证。     

5-[(3-吲哚基)-甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮衍生物的高效合成

在分子碘作用下,以吲哚、醛和2,2-二甲基-1,3-二噁烷-4,6-二酮为原料,通过三组分缩合反应合成了10种5-[(3-吲哚基)-甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮衍生物。 当催化剂的用量为5%(摩尔分数)时,30 ℃反应60~90 min,收率为71.4%~97.3%。 此外,还探讨了分子碘的催化机理。     

Synthesis, 5-hydroxytryptamine1A receptor affinity and docking studies of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives

A series of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives (12a-h) was synthesized and evaluated for binding affinity at the human 5-hydroxytryptamine(1A) receptor (5-HT(1A)R) compounds (12b) and (12h) showed the highest 5-HT(1A) receptor affinity (IC(50)=15 nM). Molecular docking studies with all the compounds in a homology model of 5-HT(1A) showed that the main interaction anchoring the ligand in the receptor was a charge-reinforced bond between the protonated nitrogen atom (N-4) of the piperazine ring and Aspartate(3.32).     

Synthesis of Substituted 3H-Indole-modified b-Cyclodextrin

The hydrophobic cavities of cyclodextrins and the inclusion with various organic molecules in the aqueous solution make them useful in chemical and biological activities1, one of which is the modified cyclodextrins acting as indicators of molecular recognition. Cyclodextrins, which are spectroscopically inert, can be converted into spectroscopically active compounds by modifing one or two of the hydroxy groups with appropriate chromophores, and used as molecular sensor due to the capability of…     

The autoxidation of 2-(2-aminophenyl)-3- methylindole

Fischer indolisation of 2-aminophenyl ethyl ketone phenylhydrazone using glacial acetic acid saturated with hydrogen chloride as catalyst affords 3-methylindolo(l′:2′-3:4)2-methylquinazoline and 2-(2-aminophenyl)-3-methylindole. The latter compound is autoxidised to 2-(2-amino-phenyl)-3-hydroxy-3-methyl-3H-indole, a reaction which is shown to be dependent upon the presence of the primary amino group at the 2-position of the 2-phenyl substituent and which is much slower than the corresponding autoxidation of 2-(2-hydroxyphenyl)-3-methylindole to 3-hydroxy-2-(2-hydroxyphenyl)-3-methyl-3H-indole previously reported.Nitration of isopropyl phenyl ketone occurs preferentially at the ortho- rather than the meta- positions of the benzene nucleus.     

Reaction of 2,3,3-trimethyl-3H-indole salts with acrylamide. Synthesis of 1,2,3,4,10,10a-hexahydropyrimido[1,2-a]indol-2-one derivatives

Methyl derivatives of pyrimido[1,2-a]indol-2-one were obtained by the reaction of 2,3,3-trimethyl-3H-indole salts with acrylamide in a proton-containing solvent. The products were condensed with aromatic aldehydes. The interconversion of pyrimido[1,2-a]indol-2-ones and 1-(2-carbamoylethyl)-3H-indolium salts under the influence of acids and bases was studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1056–1059, August, 1986.     

Prenylindoles from Tanzanian Monodora and Isolona species

6-(3-Methyl-but-2-enyl)-1,3-dihydro-indol-2-one, annonidine F [3-[6-(3-methyl-but-2-enyl)-1H-indolyl]-6-(3-methyl-but-2-enyl)-1H-indole], 1H-indole-5-carbaldehyde, 6-(3-methyl-2-butenyl)-1H-indole, 6-(3-methyl-buta-1,3-dienyl)-1H-indole, 6-(4-oxo-but-2-enyl)-1H-indole and 3-geranylindole were isolated from Monodora angolensis (Annonaceae) while 3-(1,1-dimethyl-but-2-enyl)-5-(3-methyl-but-2-enyl)-1H-indole (caulidine A), 4-[3-(1,1-dimethyl-but-2-enyl)-1H-indol-5-yl]-but-3-en-2-one (caulidine B), 5-(3-methyl-2-butenyl)-1H-indole and 5-(3-methylbuta-1,3-dienyl)-1H-indole were obtained from Isolona cauliflora (Annonaceae); structural determination by spectroscopic analysis. Some of the prenylindoles had antifungal and antimalarial activities.     

A facile preparation of 1-(6-hydroxyindol-1-yl)-2,2-dimethylpropan-1-one

An effective synthesis of 1-(6-hydroxyindol-1-yl)-2,2-dimethylpropan-1-one (4) was developed starting from 1H-indole (2). The key step involved suitable utilization of 4-(1-pyrrolidino)pyridine for the removal of the chloroacetyl moiety from chloroacetic acid 1-(2,2-dimethylpropionyl)-1H-indol-6-yl ester (3); a possible mechanism is, also, presented. Compound 4 might lead to selectively substituted derivatives, either on the phenolic-OH or the indolyl-NH, with putative biological interest. In this respect, we found that the core structure of 1H-indol-6-ol (1) possesses a degree of aldose reductase inhibitory potential, at a concentration of 100 microM.     

Experimental and Molecular Mechanical Studies of Complexation of Some 2H- and 3H- Indole Derivatives with Aqueous β-Cyclodextrin

Phase solubility diagrams (PSDs) at 25 ^∘C and molecular mechanical (MM) modeling were used to study the aqueous complexation of some 2H- and 3H-indole derivatives with β-cyclodextrin (β-CD). Among the 3H-indole derivatives investigated in this work, indole-3H-butyric acid forms the most stable 1:1 complex of the B _s -type PSD, whereas shorter chain derivatives form soluble 1:1 complexes (A _L -type PSDs) with their stability increasing as the chain length increases. Indole-2 carboxylic acid forms highly stable 1:1 and 1:2 complexes, with the lower-order complex reaching saturation first (B _s -type PSD). MM modeling indicates that the stability of the complex is highly correlated with the flexibility of the 3H-indole hydrocarbon chain, which yields a better geometrical fit within the β-CD cavity resulting from different hydrophilic interactions. These interactions are represented in the H-bonding of the carboxyl group with the primary hydroxyl group network that is situated at the narrow rim of the cavity, and also by a favorable interaction of the aromatic ring with the hydroxyl group network at the other rim.     

Solvent-free Michael addition to non-protected 3-(2-nitrovinyl)indole by ultrasound activation

A variety of nucleophiles provided by activated methylenes have been added on 3-(2-nitrovinyl)-1H-indole in very good to excellent yields, under sonication and solvent-free conditions, using solid potassium carbonate or sodium acetate as a base. Direct synthesis avoiding preliminary NH protection is reported and exemplified to 15 molecules.     

Sc(OTf)3-catalyzed or t-BuOK promoted tandem reaction of 2-(2-(alkynyl)benzylidene)malonate with indole

Tandem reaction of 2-(2-(alkynyl)benzylidene)malonate with indole was investigated. (Z)-1-Benzylidene-3-(1 H-indol-1-yl)-1 H-indene-2,2(3 H)-dicarboxylate was generated in the presence of t-BuOK at room temperature; whereas 3-((1 H-indol-3-yl)(2-(alkynyl)aryl)methyl)-1 H-indole was obtained when Sc(OTf)3 was utilized as catalyst at 50 degrees C.     

Synthesis and biological activity of N-(aminoiminomethyl)-1H-indole carboxamide derivatives as Na+/H+ exchanger inhibitors

A series of N-(aminoiminomethyl)-1H-indole carboxamide derivatives were synthesized and their inhibitory potencies against the Na+/H+ exchanger were measured. Variation of the carbonylguanidine group at the 2- to 7-position of the indole ring system showed that a substitution at the 2-position improved the Na+/H+ exchanger inhibitory activity the most in vitro. This led to the synthesis and evaluation of an extensive series of N-(aminoiminomethyl)-1H-indole-2-carboxamide derivatives. Derivatives having an alkyl or substituted alkyl group at the 1-position of the indole ring system showed higher levels of in vitro activities. N-(aminoiminomethyl)- 1-(2-phenylethyl)-1H-indole-2-carboxamide (49) had the strongest activity.