Category: 67929-86-6

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Methyl 5-methoxyindole-2-carboxylate( cas:67929-86-6 ) is researched.SDS of cas: 67929-86-6.Kasa, Anjaneyalu; Dahan, Zeyad A.; Tiwari, Girdharilal B.; Pudukulathan, Zubaidha K. published the article 《Iodine catalyzed direct regioselective 3-sulfenylation of indoles using diaryl disulfides》 about this compound( cas:67929-86-6 ) in International Journal of Research in Pharmacy and Chemistry. Keywords: indole diaryl disulfide iodine catalyst regioselective sulfenylation green chem; arylthio indole preparation. Let’s learn more about this compound (cas:67929-86-6).

A facile and simple method for synthesis of structurally diverse 3-sulfenylindole derivatives by direct sulfenylation of indoles using diaryl disulfides in the presence of mol. iodine as a catalyst. The sulfenylation proceeded well in both dichloromethane and dimethylsulfoxide. The reaction proceeded much faster in good yield in DMSO at 70°, as compared to dichloromethane at room temperature or in acetonitrile under reflux conditions and without iodine no conversion was observed With 5 mol% of iodine, a reasonable conversion was observed in dichloromethane as compared to acetonitrile at room temperature and under reflux conditions while 10 mol% gave an excellent conversion in DCM and DMSO. The simplified procedure has several merits in terms of ease of operation, mild conditions, excellent yields, atom economy and regioselectivity. The method would find wide spread application in synthesis of bioactive compounds bearing simple and substituted 3-sulfenyl moiety.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Methyl 5-methoxyindole-2-carboxylate, is researched, Molecular C11H11NO3, CAS is 67929-86-6, about [Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source, the main research direction is indole alkaloid synthesis intramol cyclization porphyrin iron catalyst; tetrahydroquinoline alkaloid synthesis intramol cyclization porphyrin iron catalyst; dihydroquinazolinone alkaloid synthesis intramol cyclization porphyrin iron catalyst; quinazolinone alkaloid synthesis intramol cyclization porphyrin iron catalyst.Electric Literature of C11H11NO3.

The syntheses of alkaloids including indoles, indolines, tetrahydroquinolines, dihydroquinazolinones and quinazolinones were accomplished in moderate to excellent yields via [Fe(F20TPP)Cl] (I) catalyzed intramol. C-N bond formation using aryl azides as nitrogen source. E.g., dihydroquinazolinone derivative II was prepared with 83% yield by refluxing N3-2-C6H4CON(CH2Ph)2 with I in (ClCH2)2.

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Reference:
Isoquinoline – Wikipedia,
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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Methoxyindoles and their derivatives, published in 1924, which mentions a compound: 67929-86-6, Name is Methyl 5-methoxyindole-2-carboxylate, Molecular C11H11NO3, Electric Literature of C11H11NO3.

2,5-O2N(HO)C6H3Me, m. 128°, was obtained in 58 g. yield (together with 42 g. of 4,5-O2N(HO)C6H3Me) by slowly adding 140 g. m-HOC6H4Me in 140 g. AcOH to a stirred mixture of 200 g. HNO3 (d. 1.5) and 400 g. AcOH at -8° to -5°, and removing the 4-NO2 derivative by steam distillation Me2SO4 (252 g.) added to 153 g. 2,5-O2N(HO)C6H3Me and 46 g. Na in 750 cc. MeOH gave a 90% yield of 2,5-O2N(MeO)C6H3Me (I), m. 55°. 2-Nitro-5-methoxyphenylpyruvic acid (II), yellow, m. 128° (phenylhydrazone, yellow, m. 151-2° (decomposition)), results in 51 g. yield from 50 g. of I and 63 g. (CO2Et)2 added to a suspn. of 35 g. EtONa in 300 cc. dry Et2O. Oxidation of II by H2O2 in 2% NaOH gave 2-nitro-5- methoxyphenylacetic acid, m. 176°. Reduction of II in NH4OH by FeSO4 gave a 73% yield of 5-methoxyindole-2-carboxylic acid (III), m. 196-7° (evolution of gas). Warmed with Ehrlich’s reagent, a deep pink color is produced, which fades on cooling. Me ester, m. 177°. Et ester, m. 156°. 2,3-O2N(MeO)C6H3Me, (CO2Et)2 and KOEt in Et2O give a 75% yield of 2-nitro-3-methoxy-phenylpyruvic acid (IV), pale yellow, m. 161-2°, or yellow with 0.5 AcOH of crystallization, m. 118-45°. The EtOH solution gives a deep green color with FeCl3, destroyed by mineral acids. Phenylhydrazone, yellow, m. 159° (decomposition). Oxidation of IV gives 2-nitro-3-methoxyphenylacetic acid, m. 137-8°, while reduction with FeSO4 and NH4OH gives 7-methoxyindole-2-carboxylic acid (V), m. 182° and decomposes on continued heating. Et ester, m. 114°. Me ester, m. 120°. 2-Nitro-6-methoxyphenylpyruvic acid (VI), yellow, m. 47-55°; phenylhydrazone, yellow, m. 173-4° (decomposition). Oxidation with H2O2 gives 2-nitro-6-methoxyphenylacetic acid, yellow, m. 172°, while reduction of VI gave 4-methoxyindole-2-carboxylic acid (VII), m. 234-5°, in 63% yield. Ehrlich’s reagent gives a purple color, which disappears on cooling. Me ester, m. 143.5°. Et ester, m. 161.5°. p-MeOC6H4NHNH2 (VIII), best prepared by diazotizing p-MeOC6H4NH2 and reducing with SnCl2 in concentrated HCl, m. 65°; yield, 44%. α-Ketobutyric acid p-methoxy-phenylhydrazone (IX), yellow, m. 105°. o-Methoxyphenylhydrazone (X), pale yellow, m. 112°. The action of concentrated H2SO4 on IX (or the components in EtOH) gives 5-methoxyskatole-2-carboxylic acid (XI), m. 200-1° (decomposition), isolated as the Et ester, m. 151-2°; Me ester, m. 156°. In the same way X gave 7-methoxyskatole-2-carboxylic acid (XII), m. 222-3°, isolated as the Me ester, m. 144-15°, the yield of the acid being only 23%. A by-product of this reaction is Et ketobutyrate phenylhydrazone, yellow, m. 59-60°. III, changed to the acid chloride by PCl5 in AcCl, this dissolved in CHCl3 and treated with MeNHCH2CH(OMe)2, gave 5-methoxyindole-2-carboxydimethylacetalyl-methylamide, m. 159°. This is converted by warming with saturated alc. HCl at 40-50° for 15 min. into a mixt, of about equal amounts of 10-methoxy-3-keto-4-methyl-3,4-dihydro-4-carboline (XIII), m. 280°, has a distinct blue fluorescence in the solid state, gives a yellow HCl salt, which is dissociated by H2O and gives no color with Ehrlich’s reagent or with vanillin and HCl in the cold; the alc. solution has a striking lilac fluorescence; and 10- methoxy-5-keto-4- methyl-4,5-dihydroindole-1,4-diazine (XIV), m. 243°, gives a greenish blue color with Ehrlich’s reagent, fading to a pale yellow on cooling and becoming green on boiling, and gives an intense purple color with vanillin and HCl; the EtOH solution has a very faint blue fluorescence which is not increased by adding HCl. 5-Methoxyindole-2-carboxyacetalylamide m. 151-2°, results from the chloride of III and H2NCH2CH(OEt)2; Ehrlich’s reagent gives a purple solution, becoming intense blue on warming, while NaNO2 produces a green color in the cold. Vanillin and HCl produce a deep pink which becomes intense bluish violet on the addition of NaNO2 and warming. The action of alc. HCl gives 10-methoxy-5-keto-4,5-dihydroindole-1,4-diazine (XV), sinters 265°, m. 280°. 5-Methoxyindole-2-carboxydimethylacetalylamide, m. 154°, and with alc. HCl gives XV. 5-Methoxyindole-2-carboxyacetalylmethylamide, m. 127°, is formed from the chloride of III and MeNHCH2CH(OEt)2; with alc. HCl it yields about equal quantities of XIII and XIV. 7- Methoxyindole-2-carboxydimethylacetalylmethylamide, obtained only as a sirup, gives with alc. HCl a mixture of approx. 4 parts 12-methoxy-3-keto-4-methyl-3,4-dihydro-4-carboline, pale yellow, m. 250°, yielding a golden-yellow HCl salt, and 1 part 12-methoxy-5-keto-4-methyl-4,5-dihydroindole-l,4-diazine, m. 135°, which gives a blue color with vanillin and HCl and a green color with Ehrlich’s solution 4-Methoxyindole-2-carboxydimethylacetalylmethylamide, m. 112°, which, with alc. HCl, gave 9-methoxy-3-keto-4-methyl-3,4-dihydro-4-carboline, m. 250°, and yields a sparingly soluble yellow HCl salt. The mother liquors gave a green color with vanillin and HCl but the diazine was not isolated. When XII was subjected to the above reactions, a compound C14H13O2N2Cl, m. 190°, was obtained, which was unchanged by treatment with 10% MeOH-KOH for 10 min. and is probably 9-chloro-12-methoxy-5-keto-4,7-dimethyl-4,5-dihydroindol-l,4-diazine. III decomposes vigorously when heated to 205-210°, yielding 5-methoxyindole (XVI), b17 176-8° m. 55°, acquires a pink tint which slowly darkens on standing, is only slightly volatile with steam (1 g. per l. of H2O), colors a pine shaving moistened with HCl reddish violet, gives a purple precipitate with concentrated HNO3 and NaNO2. Picrate, bright red, m. 145°. 1-Ac derivative (XVII), b25 210-1°, m. 80-1°. Nitration of the Ac derivative gave a mixture of an a-NO2 derivative, light brown, m. 149°, soluble in EtOH, and the b-NO2 derivative, brown, m. 213-4°, the a-derivative predominating. Hydrolysis gave a- and b-nitro-5-methoxyindoles, yellow, m. 144° (mixture m. about 112°); the a-form gives an orange-purple color with a pine stick, the b-form a deep purple. The a-form gives a pale red color with Ehrlich’s reagent, not affected by addition of NaNO2, while the b-form develops a red color only after addition of NaNO2. XVI, treated with CHCl3 and EtOH-KOH, yields a mixture of 5-methoxyindole-3-aldehyde, m. 178°, and 3-chloro-6-methoxyquinoline, m. 73-4°, separated by steam distillation XVI was also synthesized as follows: 4-Methoxy-2-aldehydophenylglycineamide oxime, yellow, m. 196° (decomposition) was obtained in 70% yield from 5,2-MeO(H2N)C6H3CH:NOH and ClCH2CONH2 (formyl derivative, bright yellow, m. 223°); on hydrolysis yields 4-methoxy-2-aldehydophenylglycine oxime, pale yellow, m. 178°; with saturated H2SO3 this is changed to 4-methoxy-2-aldehydophenylglycine, bright orange, m. 183° (decomposition) (phenylhydrazone, yellow, m. 175-6°) which yields XVII on boiling with AC2O and AcONa. V, decomposed at 230-3°, gives 73% of 7-methoxyindole, b17 157°, b21 159-61°, slowly turns brown on keeping, fairly volatile with steam (2 g. per 500 cc. H2O), gives a deep mauve pine-shaving reaction, gives a yellow color with Ehrlich’s reagent, deepening to orange-red on warming and to a deep reddish purple on addition of dilute NaNO2. Picrate, red, m. 156°. With alc. KOH and CHCl3 this yields 7-methoxyindole-3-aldehyde, m. 159-60°, and 3-chloro-8-methoxyquinoline, m. 84.5°; the yield of both products was small. VII, at 245-50°, gives 4-methoxyindole, m. 69.5°, (picrate, red, m. 159-60°) gives a deep purple pine-shaving reaction and a reddish purple color with Ehrlich’s reagent. XI decomposes at 210° and gives 75% of 5-methoxyskatole, m. 66°, apparently non-volatile with steam, gives a red pine-shaving reaction and a reddish purple color with Ehrlich’s reagent. Picrate, dark red, m. 151-2°. XII similarly yields 7-methoxyskatole, b20 170° (picrate, brownish red, m. 156°). The pine-shaving reaction is a deep purplish red; Ehrlich’s reagent gives no color in the cold; on warming a reddish purple color develops. The K derivative of II gives with Me2SO4 2-nitro-α-methoxycinnamic acid (XVIII), pale yellow, m. 164-5°. Na salt, yellow. Me ester, pale yellow, m. 67°; the Et ester appears to be an oil. Oxidation of XVIII gives o-O2NC6H4CHO. Reduction of XVIII with FeSO4 and NH4OH gives the 2-amino derivative, pale yellow, crystallines with 2AcOH and m. 167°. Me ester, yellow, m. 60-1°. The acid readily loses MeOH, forming indole-2-carboxylic acid, m. 203-4° (heating above its m. p., solution in cold concentrated H2SO4 at room temperature for 16 hrs., boiling with 10% HCl or reduction of XVIII with FeSO4 and NH4OH and boiling the reaction product for 24 hrs.). 2-Nitro-α,3-dimethoxycinnamic acid, from IV, as above, m. 202° (decomposition), and reduced to the 2-amino derivative, m. 139°, and decomposing above its m. p. to give V.

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Isoquinoline – Wikipedia,
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Praveen, Chandrasekaran; Ayyanar, Asairajan; Perumal, Paramasivan Thirumalai published the article 《Gold(III) chloride catalyzed regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones and evaluation of anticancer potential towards human cervix adenocarcinoma》. Keywords: pyranoindolone preparation anticancer; iodoindolecarboxylate preparation alkyne cross coupling hydrolysis cycloisomerization gold catalyst.They researched the compound: Methyl 5-methoxyindole-2-carboxylate( cas:67929-86-6 ).Category: isoquinoline. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:67929-86-6) here.

A highly regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones via gold(III) chloride catalyzed cycloisomerization of 3-ethynyl-indole-2-carboxylic acid was achieved in good to excellent yields. These compounds were screened for their in vitro cytotoxicity against human cervical (HeLa) cell lines. Out of ten compounds, three compounds I (R = Me, Et, H) showed comparable proliferation inhibitory activity against the standard drug cisplatin. Compound I (r = Me) was found to be the most efficacious with IC50 value of 0.22 μM.

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Isoquinoline – Wikipedia,
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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 67929-86-6, is researched, Molecular C11H11NO3, about Arylthioindoles, Potent Inhibitors of Tubulin Polymerization, the main research direction is arylthioindole preparation tubulin polymerization inhibitor.Related Products of 67929-86-6.

Several arylthioindoles had excellent activity as inhibitors both of tubulin polymerization and of the growth of MCF-7 human breast carcinoma cells. Me 3-[(3,4,5-trimethoxyphenyl)thio]-5-methoxy-1H-indole-2-carboxylate (I), the most potent derivative, showed IC50 = 2.0 μM, 1.6 times more active than colchicine and about as active as combretastatin A-4 (CSA4). Compound I inhibited the growth of the MCF-7 cells at IC50 = 13 nM. Colchicine and CSA4 had 13 nM and 17 nM IC50 values, resp., with these cells.

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Preti, Delia; Romagnoli, Romeo; Rondanin, Riccardo; Cacciari, Barbara; Hamel, Ernest; Balzarini, Jan; Liekens, Sandra; Schols, Dominique; Estevez-Sarmiento, Francisco; Quintana, Jose; Estevez, Francisco published an article about the compound: Methyl 5-methoxyindole-2-carboxylate( cas:67929-86-6,SMILESS:O=C(C(N1)=CC2=C1C=CC(OC)=C2)OC ).Reference of Methyl 5-methoxyindole-2-carboxylate. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:67929-86-6) through the article.

Inhibition of microtubule function using tubulin targeting agents has received growing attention in the last several decades. The indole scaffold has been recognized as an important scaffold in the design of novel compounds acting as antimitotic agents. Indole-based chalcones, in which one of the aryl rings was replaced by an indole, have been explored in the last few years for their anticancer potential in different cancer cell lines. Eighteen novel (3′,4′,5′-trimethoxyphenyl)-indolyl-propenone derivatives with general structure were synthesized and evaluated for their antiproliferative activity against a panel of four different human cancer cell lines. The highest IC50 values were obtained against the human promyelocytic leukemia HL-60 cell line. This series of chalcone derivatives was characterized by the presence of a 2-alkoxycarbonyl indole ring as the second aryl system attached at the carbonyl of the 3-position of the 1-(3′,4′,5′-trimethoxyphenyl)-2-propen-1-one framework. The structure-activity relationship (SAR) of the indole-based chalcone derivatives was investigated by varying the position of the methoxy group, by the introduction of different substituents (hydrogen, Me, Et or benzyl) at the N-1 position and by the activity differences between methoxycarbonyl and ethoxycarbonyl moieties at the 2-position of the indole nucleus. The antiproliferative activity data of the novel synthesized compounds revealed that generally N-substituted indole analogs exhibited considerably reduced potency as compared with their parent N-unsubstituted counterparts, demonstrating that the presence of a hydrogen on the indole nitrogen plays a decisive role in increasing antiproliferative activity. The results also revealed that the position of the methoxy group on the indole ring is a critical determinant of biol. activity. Among the synthesized derivatives, compound , containing the 2-methoxycarbonyl-6-methoxy-N-1H-indole moiety exhibited the highest antiproliferative activity, with IC50 values of 0.37, 0.16 and 0.17 μM against HeLa, HT29 and MCF-7 cancer cell lines, resp., and with considerably lower activity against HL-60 cells (IC50: 18 μM). This derivative also displayed cytotoxic properties (IC50 values ∼1 μM) in the human myeloid leukemia U-937 cell line overexpressing human Bcl-2 (U-937/Bcl-2) via cell cycle progression arrest at the G2-M phase and induction of apoptosis. The results obtained also demonstrated that the antiproliferative activity of this mol. is related to inhibition of tubulin polymerization The presence of a methoxy group at the C5- or C6-position of the indole nucleus, as well as the absence of substituents at the N-1-indole position, contributed to the optimal activity of the indole-propenone-3′,4′,5′-trimethoxyphenyl scaffold.

The article 《Design, synthesis, in vitro antiproliferative activity and apoptosis-inducing studies of 1-(3′,4′,5′-trimethoxyphenyl)-3-(2′-alkoxycarbonylindolyl)-2-propen-1-one derivatives obtained by a molecular hybridisation approach》 also mentions many details about this compound(67929-86-6)Reference of Methyl 5-methoxyindole-2-carboxylate, you can pay attention to it, because details determine success or failure

Reference:
Isoquinoline – Wikipedia,
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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called A highly efficient procedure for 3-sulfenylation of indole-2-carboxylates, published in 2004-03-04, which mentions a compound: 67929-86-6, mainly applied to indole carboxylate sulfenylation; thioindole preparation; amide indol preparation cyclization; thiazepinoindolone preparation, Application of 67929-86-6.

A highly efficient one-pot procedure for 3-sulfenylation of 2-carboxyindoles is described. Treatment of thiols with N-chlorosuccinimide at -78 °C in CH2Cl2 affords sulfenyl chlorides in situ that readily react with 2-carboxyindoles to give 3-thioindoles in high yields. This new method is milder, produces less waste, and is compatible with a wide range of thiol and indole functionality.

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Isoquinoline – Wikipedia,
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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Coluccia, Antonio; Puxeddu, Michela; Nalli, Marianna; Wei, Chih-Ku; Wu, Yu-Hsuan; Mastrangelo, Eloise; Mohmmed, Tasneem; Tarantino, Delia; Bugert, Joachim Jakob; Schreiner, Benno; Nolte, Juliane; Schwarze, Frank; La Regina, Giuseppe; Lee, Jin-Ching; Silvestri, Romano researched the compound: Methyl 5-methoxyindole-2-carboxylate( cas:67929-86-6 ).Related Products of 67929-86-6.They published the article 《Discovery of Zika Virus NS2B/NS3 Inhibitors That Prevent Mice from Life-Threatening Infection and Brain Damage》 about this compound( cas:67929-86-6 ) in ACS Medicinal Chemistry Letters. Keywords: preparation Zika virus NS2B NS3 inhibitor brain. We’ll tell you more about this compound (cas:67929-86-6).

Zika virus (ZIKV) infection, which initially was endemic only in Africa and Asia, is rapidly spreading throughout Europe, Oceania, and the Americas. Although there have been enormous efforts, there is still no approved drug to treat ZIKV infection. Herein, we report the synthesis and biol. evaluation of agents with noncompetitive mechanism of the ZIKV NS2B/NS3 protease inhibition through the binding to an allosteric site. Compounds 1 and 2 showed potent activity in both enzymic and cellular assays. Derivative 1 efficiently reduced the ZIKV protein synthesis and the RNA replication and prevented the mice from life-threatening infection and the brain damage caused by ZIKV infection in a ZIKV mouse model.

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 67929-86-6, is researched, SMILESS is O=C(C(N1)=CC2=C1C=CC(OC)=C2)OC, Molecular C11H11NO3Journal, Article, Research Support, Non-U.S. Gov’t, Chemical Communications (Cambridge, United Kingdom) called Continuous flow thermolysis of azidoacrylates for the synthesis of heterocycles and pharmaceutical intermediates, Author is O’Brien, Alexander G.; Levesque, Francois; Seeberger, Peter H., the main research direction is continuous flow thermolysis azidoacrylate; indole preparation; heterocycle preparation.Quality Control of Methyl 5-methoxyindole-2-carboxylate.

An efficient, safe and scalable procedure for the continuous flow thermolysis of azidoacrylates to yield indoles has been developed and was applied to the synthesis of related heterocycles. The scalability of the process was demonstrated in the continuous flow synthesis of a precursor to the DAAO inhibitor 4H-furo[3,2-b]pyrrole-5-carboxylic acid.

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Isoquinoline – Wikipedia,
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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Methyl 5-methoxyindole-2-carboxylate, is researched, Molecular C11H11NO3, CAS is 67929-86-6, about Design, synthesis and biological evaluation of 2-alkoxycarbonyl-3-anilinoindoles as a new class of potent inhibitors of tubulin polymerization, the main research direction is alkoxycarbonyl anilinoindole preparation docking tubulin polymerization SAR antiproliferative human; Antiproliferative activity; Indole; Microtubules; Structure-activity relationship; Tubulin.Recommanded Product: Methyl 5-methoxyindole-2-carboxylate.

A new class of inhibitors of tubulin polymerization based on 2-alkoxycarbonyl-3-(3′,4′,5′-trimethoxyanilino)indole mol. skeleton I [R1 = H, 6-Cl, 5-MeO, etc.; R2 = Me, Et, iso-Pr, etc.; R3 = Me, Et, n-Pr, Bn; X = H, MeO] was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization and cell cycle effects. The results presented show that methoxy substitution and location on indole nucleus played an important role in inhibition of cell growth, and the most favorable position for substituent was at C-6. In addition, a small-size ester function (methoxy/ethoxycarbonyl) at 2-position of the indole core was desirable. Also, analogs that were alkylated with Me, Et or Pr groups or had a benzyl moiety on the N-1 indolic nitrogen retained activity equivalent to those observed in the parent N-1H analogs. The most promising compounds of series I [R1 = 5-MeO, R2 = Me, R3 = H, X = H; R1 = 6-MeO, R2 = R3 = Me, X = MeO] targeted tubulin at colchicine site with antitubulin activities comparable to that of reference compound combretastatin A-4.

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