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6,7-去环氧-6,7-二去氢-5-脱氧-21-去苯基-21-(苯基甲基)瑞香毒素 | 57852-42-3

分子结构分类

有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质

中文名称

6,7-去环氧-6,7-二去氢-5-脱氧-21-去苯基-21-(苯基甲基)瑞香毒素

中文别名

Resiniferonol 9,13,14-ortho-乙酸苯酯

英文名称

resiniferonol 9,13,14-ortho-phenylacetate

英文别名

Ropa；(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-8-(hydroxymethyl)-4,17-dimethyl-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-5-one

6,7-去环氧-6,7-二去氢-5-脱氧-21-去苯基-21-(苯基甲基)瑞香毒素化学式

CAS

57852-42-3

化学式

C₂₈H₃₂O₆

mdl

——

分子量

464.558

InChiKey

FFKXTXJQZGIKQZ-WAGMVDSNSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

2.7
重原子数：

34
可旋转键数：

4
环数：

6.0
sp3杂化的碳原子比例：

0.54
拓扑面积：

85.2
氢给体数：

2
氢受体数：

6

SDS

SDS：7a37806eabffd65000b842ec53e23851

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制备方法与用途

ROPA，也称为Resiniferonol 9,13,14-ortho-phenylacetate，是一种强效的PKCα和PKCγ激活剂，通过PKC活化促进肿瘤生长。

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl benzoate	83117-41-3	C₃₅H₃₆O₇	568.667
——	(1R,2S,4S,6R,10S,11R,13S,15R,17R)-13-benzyl-8-(hydroxymethyl)-4,17-dimethyl-15-prop-1-en-2-yl-6-trimethylsilyloxy-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadec-8-en-5-one	200265-05-0	C₃₁H₄₂O₆Si	538.756
——	[(1R,2S,6R,10S,11R,13S,15R,17R)-13-benzyl-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-6-trimethylsilyloxy-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl benzoate	200265-06-1	C₃₈H₄₄O₇Si	640.849
——	[(1R,2S,4S,6R,10S,11R,13S,15R,17R)-13-benzyl-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-6-trimethylsilyloxy-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadec-8-en-8-yl]methyl benzoate	200265-20-9	C₃₈H₄₆O₇Si	642.865
——	(1R,2S,4S,5Z,6R,8S,10S,11R,14R)-5-benzylidene-8-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,14-dimethyl-11-phenylmethoxy-6-trimethylsilyloxy-15-oxatetracyclo[6.6.1.01,10.02,6]pentadecan-12-one	184151-85-7	C₄₀H₅₈O₅Si₂	675.069
——	(1R,2R,4S,8R,9S,11S,13R,15S,17S)-4-acetyl-11-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,15-dimethyl-13-trimethylsilyloxy-5,7,18-trioxapentacyclo[9.6.1.01,9.04,8.013,17]octadecane-6,14-dione	200264-98-8	C₂₉H₄₈O₈Si₂	580.866

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl benzoate	83117-41-3	C₃₅H₃₆O₇	568.667
超强辣素	resiniferatoxin	57444-62-9	C₃₇H₄₀O₉	628.719
——	(4-amino-3-methoxyphenyl) [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl carbonate	1470111-38-6	C₃₆H₃₉NO₉	629.707
——	[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^{1,10}.0^{2,6}.0^{11,15}]octadeca-3,8-dien-8-yl]methyl (4-hydroxy-3-iodo-5-methoxyphenyl) carbonate	1208246-58-5	C₃₆H₃₇IO₁₀	756.588
——	[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl (3-chloro-4-hydroxy-5-methoxyphenyl) carbonate	1470111-31-9	C₃₆H₃₇ClO₁₀	665.137
——	[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl (3-fluoro-4-hydroxy-5-methoxyphenyl) carbonate	1470111-29-5	C₃₆H₃₇FO₁₀	648.682
——	[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl (3-bromo-4-hydroxy-5-methoxyphenyl) carbonate	1470111-33-1	C₃₆H₃₇BrO₁₀	709.588
——	(4-amino-3-fluoro-5-methoxyphenyl) [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl carbonate	1470111-42-2	C₃₆H₃₈FNO₉	647.697
——	(4-amino-3-iodo-5-methoxyphenyl) [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl carbonate	1470111-48-8	C₃₆H₃₈INO₉	755.604
——	(4-amino-3-chloro-5-methoxyphenyl) [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl carbonate	1470111-44-4	C₃₆H₃₈ClNO₉	664.152
——	(4-amino-3-bromo-5-methoxyphenyl) [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl carbonate	1470111-46-6	C₃₆H₃₈BrNO₉	708.603
——	[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl [4-(methanesulfonamido)-3-methoxyphenyl] carbonate	1470111-40-0	C₃₇H₄₁NO₁₁S	707.799
——	[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-acetyloxy-2-iodo-5-methoxyphenyl)acetate	412271-86-4	C₃₉H₄₁IO₁₀	796.653

反应信息

作为反应物：

描述：

6,7-去环氧-6,7-二去氢-5-脱氧-21-去苯基-21-(苯基甲基)瑞香毒素在四氢吡咯、 4-二甲氨基吡啶作用下，以二氯甲烷、甲苯为溶剂，生成超强辣素

参考文献：

名称：

达芬烷二萜的首次合成：(+)-树脂毒素的对映控制全合成

摘要：

Resiniferatoxin (RTX,1) 是一种达芬烷二萜，根据其非凡的刺激活性在大戟属的乳胶中鉴定。1 虽然在结构上与有效的促肿瘤佛波酯相关，但 2 RTX 不是肿瘤启动子 3 并且不竞争蛋白激酶 C 上的佛波酯结合位点。 4 然而，它确实表现出与辣椒素相同的活性 (2 )，红辣椒的主要活性成分。5 除了广受好评的烹饪用途外，辣椒素还是多种商业镇痛剂配方中的活性成分，并且作为镇痛剂和拒食剂也很受关注。6 在许多测定中表现出比辣椒素高 10 3 到 105 倍的效力，RTX 本身作为镇痛剂具有特殊的治疗意义，特别适用于治疗与糖尿病性多发性神经病和带状疱疹后遗神经痛相关的疼痛。7 此外，RTX 及其类似物可作为研究相对较少的香草素受体的生化研究的关键探针。8 尽管达芙妮提取物的持续治疗使用时间非常长（> 2000 年）， 5a 达芙妮及其类似物的复杂性和有限的可用性极大地限制了对其分子作用模式的研究。9

DOI：

10.1021/ja972279y
作为产物：

描述：

(2R,4S,5R)-5-Benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-4-hydroxy-2-methyl-hept-6-en-1-one 在 palladium dihydroxide 、 palladium on activated charcoal 、四丙基高氯酸铵吡啶、三乙烯二胺、咪唑、叔丁基过氧化氢、 4-二甲氨基吡啶、 manganese(IV) oxide 、 barium dihydroxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 selenium(IV) oxide 、氯化亚砜、高氯酸、 N-甲基吲哚酮、 18-冠醚-6 、 dibutylbis(cyclopentadienyl)zirconium 、氢氟酸、四丁基氟化铵、氢气、 silver benzoate 、四丁基碘化铵、臭氧、 1,8-二氮杂双环[5.4.0]十一碳-7-烯、间氯过氧苯甲酸、 methyloxirane 、 lithium bromide 、锌作用下，以四氢呋喃、 1,4-二氧六环、甲醇、六甲基磷酰三胺、乙醚、乙醇、二氯甲烷、乙酸乙酯、甲苯、乙腈为溶剂， -78.0~150.0 ℃ 、337.84 kPa 条件下，反应 4.0h，生成 6,7-去环氧-6,7-二去氢-5-脱氧-21-去苯基-21-(苯基甲基)瑞香毒素

参考文献：

名称：

达芬烷二萜的首次合成：(+)-树脂毒素的对映控制全合成

摘要：

Resiniferatoxin (RTX,1) 是一种达芬烷二萜，根据其非凡的刺激活性在大戟属的乳胶中鉴定。1 虽然在结构上与有效的促肿瘤佛波酯相关，但 2 RTX 不是肿瘤启动子 3 并且不竞争蛋白激酶 C 上的佛波酯结合位点。 4 然而，它确实表现出与辣椒素相同的活性 (2 )，红辣椒的主要活性成分。5 除了广受好评的烹饪用途外，辣椒素还是多种商业镇痛剂配方中的活性成分，并且作为镇痛剂和拒食剂也很受关注。6 在许多测定中表现出比辣椒素高 10 3 到 105 倍的效力，RTX 本身作为镇痛剂具有特殊的治疗意义，特别适用于治疗与糖尿病性多发性神经病和带状疱疹后遗神经痛相关的疼痛。7 此外，RTX 及其类似物可作为研究相对较少的香草素受体的生化研究的关键探针。8 尽管达芙妮提取物的持续治疗使用时间非常长（> 2000 年）， 5a 达芙妮及其类似物的复杂性和有限的可用性极大地限制了对其分子作用模式的研究。9

DOI：

10.1021/ja972279y

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文献信息

Synthesis and in vitro evaluation of a novel iodinated resiniferatoxin derivative that is an agonist at the human vanilloid VR1 receptor

作者：Mark E. McDonnell、Sui-Po Zhang、Adrienne E. Dubin、Scott L. Dax

DOI：10.1016/s0960-894x(02)00127-0

日期：2002.4

Using a 'directed' iodination procedure, novel iodo-resiniferatoxin congeners were synthesized from 4-acetoxy-3-methoxyphenylacetic acid and resiniferinol- 9.13,14-ortho-phenylacetate (ROPA). The 2-iodo-4-hydroxy-5-methoxyphenlacetic acid ester of resiniferinol 5 displayed high affinity binding (K-i=0.71 nM) for the human vanilloid VR1 receptor and functioned as a partial agonist. (C) 2002 Elsevier Science Ltd. All rights reserved.
Structure–activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The homovanillyl moiety

作者：Giovanni Appendino、Abdellah Ech-Chahad、Alberto Minassi、Sara Bacchiega、Luciano De Petrocellis、Vincenzo Di Marzo

DOI：10.1016/j.bmcl.2006.09.077

日期：2007.1

Starting from ROPA (2), analogues of RTX (1a) modified on the acyl side chain were prepared and evaluated for vanilloid activity in HEK-293 cells over-expressing the human recombinant TRPV1. The ROPA motif provided an enhancement of potency sufficient to expand the range of vanillyl surrogates to structural elements (e.g., an unsubstituted phenyl ring) that afford inactive analogues in compounds from the capsaicin series. (c) 2006 Elsevier Ltd. All rights reserved.
The carbonate analogues of 5′-halogenated resiniferatoxin as TRPV1 ligands

作者：Kwang Su Lim、Hobin Lee、Sung Eun Kim、Tae-Hwan Ha、Jihyae Ann、Karam Son、Sun Choi、Wei Sun、Larry V. Pearce、Ian A. DeAndrea-Lazarus、Peter M. Blumberg、Jeewoo Lee

DOI：10.1016/j.ejmech.2013.07.042

日期：2013.10

A series of carbonate analogues of 5'-halogenated RTX have been investigated in order to examine the effect of the carbonate group as a linker and the role of halogens in the reversal of activity from agonism to antagonism for rat and human TRPV1 heterologously expressed in Chinese hamster ovary cells. The carbonate analogues showed similar activities to the corresponding RTX derivatives in rat TRPV1 but lower potency in human TRPV1. 5-Halogenation converted the agonists to partial agonists or full antagonists and the extent of antagonism reflected the order of I > Br > Cl > F, with a somewhat greater extent of antagonism for the derivatives of the 4-amino RTX surrogates compared to the corresponding derivatives of RTX itself. The carbonate analogues of I-RTX: (60) and 5-bromo-4-amino-RTX (66) were potent and full antagonists with K-i(ant) = 2.23 and 2.46 nM, respectively, for rat TRPV1, which were ca. 5-fold more potent than I-RTX (2) under our conditions. The conformational analysis of the I-RTX-carbonate (60) indicated that its bent conformation was similar to that of I-RTX, consistent with compound 60 and I-RTX showing comparable potent antagonism. (C) 2013 Elsevier Masson SAS. All rights reserved.
Non-vanillyl resiniferatoxin analogues as potent and metabolically stable transient receptor potential vanilloid 1 agonists

作者：Hyun-Kyung Choi、Sun Choi、Yoonji Lee、Dong Wook Kang、HyungChul Ryu、Han-Joo Maeng、Suk-Jae Chung、Vladimir A. Pavlyukovets、Larry V. Pearce、Attila Toth、Richard Tran、Yun Wang、Matthew A. Morgan、Peter M. Blumberg、Jeewoo Lee

DOI：10.1016/j.bmc.2008.11.085

日期：2009.1

A series of non-vanillyl resiniferatoxin analogues, having 4-methylsulfonylaminophenyl and fluorophenyl moieties as vanillyl surrogates, have been investigated as ligands for rat TRPV1 heterologously expressed in Chinese hamster ovary cells. Although lacking the metabolically problematic 4-hydroxy substituent on the A-region phenyl ring, the compounds retained substantial agonist potency. Indeed, the 3-methoxy-4-methylsulfonylaminophenyl analog (1) was modestly (2.5-fold) more potent than RTX, with an EC50 = 0.106 nM. Further, it resembled RTX in its kinetics and pattern of stimulation of the levels of intracellular calcium in individual cells, as revealed by imaging. Compound 1 displayed modestly enhanced in vitro stability in rat liver microsomes and in plasma, suggesting that it might be a pharmacokinetically more favorable surrogate of resiniferatoxin. Molecular modeling analyses with selected analogues provide evidence that the conformational differences could affect their binding affinities, especially for the ester versus amide at the B-region. (C) 2008 Elsevier Ltd. All rights reserved.
Eur. J. Org. Chem. 2002, 71-78

作者：

DOI：——

日期：——