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2-[(3Z)-6-氟-2-甲基-3-[(4-甲基磺酰基苯基)亚甲基]茚-1-基]乙酸 | 59973-80-7

分子结构分类

有机化合物 - 苯类化合物 - 茚和异茚

中文名称

2-[(3Z)-6-氟-2-甲基-3-[(4-甲基磺酰基苯基)亚甲基]茚-1-基]乙酸

中文别名

——

英文名称

sulindac sulfone

英文别名

exisulind；sulindac；(Z)-5-Fluoro-2-methyl-1-(p-methylsulfonylbenzylidene)-inden-3-ylacetic acid；2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfonylphenyl)methylidene]inden-1-yl]acetic acid

2-[(3Z)-6-氟-2-甲基-3-[(4-甲基磺酰基苯基)亚甲基]茚-1-基]乙酸化学式

CAS

59973-80-7

化学式

C₂₀H₁₇FO₄S

mdl

——

分子量

372.417

InChiKey

MVGSNCBCUWPVDA-MFOYZWKCSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

248-250°C
比旋光度：

D -62° (c = 1 in CHCl3)
溶解度：

二甲基亚砜：>25 mg/mL

计算性质

辛醇/水分配系数(LogP)：

3.5
重原子数：

26
可旋转键数：

4
环数：

3.0
sp3杂化的碳原子比例：

0.15
拓扑面积：

79.8
氢给体数：

1
氢受体数：

5

安全信息

WGK Germany：

3
危险性防范说明：

P261,P305+P351+P338
危险性描述：

H302,H315,H319,H335
储存条件：

-20°C

SDS

SDS：17c5e2af6a3851cb06f64735e6f15587

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制备方法与用途

Sulindac sulfone 是一种mTORC1途径的抑制剂，同时也是磺胺类药物硫辛酸的代谢产物。它能够抑制结肠癌细胞的生长，并诱导细胞周期停滞，在癌症研究中具有应用价值。

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
——	Sulindac	38194-50-2	C₂₀H₁₇FO₃S	356.418
(S)-舒林酸	(S)-Sulindac sulfoxide	149116-77-8	C₂₀H₁₇FO₃S	356.418
(R)-舒林酸	(R)-sulindac	190967-68-1	C₂₀H₁₇FO₃S	356.418
硫化舒林酸	sulindac sulfide	49627-27-2	C₂₀H₁₇FO₂S	340.418

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	methyl 2-((1Z)-1-(4-(methylsulfonyl)benzylidene)-5-fluoro-2-methyl-1H-inden-3-yl)acetate	141741-24-4	C₂₁H₁₉FO₄S	386.444
——	(Z)-4-hydroxybutyl 2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetate	1538580-45-8	C₂₄H₂₅FO₅S	444.524
——	(Z)-2-(nitrooxy)ethyl 2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetate	1538580-35-6	C₂₂H₂₀FNO₇S	461.468
——	(Z)-4-(nitrooxy)butyl 2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetate	——	C₂₄H₂₄FNO₇S	489.521
——	(Z)-6-(nitrooxy)hexyl 2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetate	1538580-36-7	C₂₆H₂₈FNO₇S	517.575
——	(Z)-5-fluoro-2-methyl-1-[[4-(methylsulfone)phenyl]methylene]-1H-indene-3-acetic acid 2-methanesulfonylsulfanylethyl ester	917471-50-2	C₂₃H₂₃FO₆S₃	510.628
——	(Z)-1,3-bis(nitrooxy)propan-2-yl 2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetate	1538580-37-8	C₂₃H₂₁FN₂O₁₀S	536.492
——	(Z)-3-(nitrooxy)-2,2-bis((nitrooxy)methyl)propyl 2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetate	1538580-38-9	C₂₅H₂₄FN₃O₁₃S	625.542
——	(E)-2-(6-fluoro-2-methyl-3-(4-(methylsulfonyl)benzylidene)-3H-inden-1-yl)acetic acid O-(tert-butyldimethylsilyl)hydroxyamide	——	C₂₆H₃₂FNO₄SSi	501.694
——	(Z)-5-fluoro-2-methyl-1-[[4-(methylsulfone)phenyl]methylene]-1H-indene-3-acetic acid 4-(thioxo-5H-[1,2]dithiol-3-yl)-phenyl ester	917471-48-8	C₂₉H₂₁FO₄S₄	580.746
——	(Z)-4-(4-(2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)butoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide	1538580-66-3	C₃₂H₂₉FN₂O₉S₂	668.721
——	(Z)-4-(2-(2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide	1538580-64-1	C₃₀H₂₅FN₂O₉S₂	640.667
——	(Z)-4-(3-(2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)propoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide	1538580-65-2	C₃₁H₂₇FN₂O₉S₂	654.694
——	4-(((Z)-4-(2-((Z)-5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)but-2-en-1-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide	1538580-70-9	C₃₂H₂₇FN₂O₉S₂	666.705
——	(Z)-4-(2-(2-(2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)ethoxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide	1538580-68-5	C₃₂H₂₉FN₂O₁₀S₂	684.72
——	(Z)-4-((6-(2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)hexyl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide	1538580-67-4	C₃₄H₃₃FN₂O₉S₂	696.774
——	(Z)-4-((4-(2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)but-2-yn-1-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide	1538580-69-6	C₃₂H₂₅FN₂O₉S₂	664.689
——	(Z)-4-(3-(2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)phenoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide	1538580-72-1	C₃₄H₂₅FN₂O₉S₂	688.711
——	(Z)-4-(3-((2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)methyl)phenoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide	1538580-71-0	C₃₅H₂₇FN₂O₉S₂	702.738

反应信息

作为反应物：

描述：

2-[(3Z)-6-氟-2-甲基-3-[(4-甲基磺酰基苯基)亚甲基]茚-1-基]乙酸在 N,N'-羰基二咪唑作用下，以二氯甲烷、乙腈为溶剂，反应 30.0h，生成 N-((2-(2-((Z)-5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetamido)ethoxy)carbamoyl)-3-phenylsydnonimine

参考文献：

名称：

Synthesis and biological evaluation of nitric oxide-donating analogues of sulindac for prostate cancer treatment

摘要：

A series of analogues of the non-steroidal anti-inflammatory drug (NSAID) sulindac 1 were synthesised tethered to nitric oxide (NO) donating functional groups. Sulindac shows antiproliterative effects against immortal PC3 cell lines. It was previously demonstrated that the effect can be enhanced when tethered to NO releasing groups such as nitrate esters, furoxans and sydnonimines. To explore this approach further, a total of fifty-six sulindac-NO analogues were prepared and they were evaluated as NO-releasing cytotoxic agents against prostate cancer (PCa) cell lines. Compounds 1k and 1n exhibited significant cytotoxic with IC50 values of 6.1 +/- 4.1 and 12.1 +/- 3.2 mu M, respectively, coupled with observed nitric oxide release. (C) 2013 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.bmc.2013.12.014
作为产物：

描述：

Sulindac 在 Oxone 作用下，以四氢呋喃、甲醇、水为溶剂，反应 24.0h，以75%的产率得到2-[(3Z)-6-氟-2-甲基-3-[(4-甲基磺酰基苯基)亚甲基]茚-1-基]乙酸

参考文献：

名称：

舒林酸异羟肟酸对人胰腺癌和结肠癌细胞的治疗潜力

摘要：

非甾体抗炎药（NSAID）舒林酸在人类癌症中表现出环加氧酶（COX）依赖性和COX依赖性化学预防特性。本研究旨在研究用异羟肟酸取代羧酸基团是否可以增强舒林酸的体外抗肿瘤和抗血管生成活性。这项研究中使用的表征工具包括细胞活力分析，胱天蛋白酶3/7诱导，DNA片段化和基因表达。我们的研究结果表明，新合成的舒林酸异羟肟酸衍生物及其砜和硫化物代谢物的功效对人胰腺癌和结肠癌细胞具有良好的抗癌活性（IC 50平均值从6±1.1μM到64 ±1.1μM）和功效（Ë最大〜100％）。异羟肟酸衍生物比羧酸对应物触发更高程度的凋亡，增加bax / bcl-2表达比并诱导caspase 3/7活化。最值得注意的是，这些化合物在亚微摩尔浓度下显着抑制了促血管生成生长因子刺激的血管内皮细胞（HUVEC）的增殖。我们的数据还提供了证据，舒林酸异羟肟酸的COX活性代谢产物是该系列中最活跃的，选择性抑制COX-1而不是C

DOI：

10.1016/j.ejmech.2010.08.019

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文献信息

MODIFICATION OF DRUGS FOR INCORPORATION INTO NANOPARTICLES

申请人：UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.

公开号：US20170087167A1

公开（公告）日：2017-03-30

Aspirin is chemically modified to generate a prodrug that releases aspirin in cellular milieu. The prodrug has a lipophilic tail that may enhance uptake efficiency in nanoparticles. Nanoparticles including the prodrugs may be effective for treating inflammatory disorders, including neurodegenerative disorders.

阿司匹林经过化学修饰，生成了一种前药，该前药能够在细胞环境中释放阿司匹林。这种前药具有亲脂性尾部，可能增强纳米颗粒中的摄取效率。包含这些前药的纳米颗粒可能对治疗炎症性疾病有效，包括神经退行性疾病。
PHOSPHO-ESTER DERIVATIVES AND USES THEREOF

申请人：RIGAS Basil

公开号：US20130225529A1

公开（公告）日：2013-08-29

Phospho-ester compounds and pharmaceutical compositions thereof administered by the respiratory and other routes for the prevention and/or treatment of lung and brain cancer and precancerous conditions thereof, for the treatment of pain, for the treatment of skin disorders, for treating and/or preventing inflammation-related diseases, and for the treatment and prevention of cancer.

磷酸酯化合物及其制剂可通过呼吸道及其他途径用于预防和/或治疗肺癌和脑癌及其癌前病变条件，用于疼痛治疗，用于皮肤疾病治疗，用于治疗和/或预防与炎症相关的疾病，以及用于癌症的治疗和预防。
Diverse amide analogs of sulindac for cancer treatment and prevention

作者：Bini Mathew、Judith V. Hobrath、Michele C. Connelly、R. Kiplin Guy、Robert C. Reynolds

DOI：10.1016/j.bmcl.2017.09.022

日期：2017.10

Sulindac is a non-steroidal anti-inflammatory drug (NSAID) that has shown significant anticancer activity. Sulindac sulfide amide (1) possessing greatly reduced COX-related inhibition relative to sulindac displayed in vivo antitumor activity that was comparable to sulindac in a human colon tumor xenograft model. Inspired by these observations, a panel of diverse sulindac amide derivatives have been

舒林酸是一种非甾体抗炎药（NSAID），已显示出显着的抗癌活性。相对于舒林酸，舒林酸硫化物酰胺（1）具有大大降低的COX相关抑制作用，在人结肠肿瘤异种移植模型中具有与舒林酸相当的体内抗肿瘤活性。受这些观察结果的启发，已经合成了一组不同的舒林酸酰胺衍生物，并针对三种癌细胞系（前列腺癌，结肠癌和乳腺癌）探测了它们的活性。鉴定出一种中性类似物化合物79具有相对于铅1相当的效力，并且对一组淋巴细胞性白血病细胞系具有活性。相对于父系，几个新系列也表现出良好的活动性（1），包括五个类似的类似物，它们也具有针对急性淋巴细胞白血病细胞的纳摩尔抑制力。鉴定出的几种新的类似物可作为抗癌药物的潜在候选者，以进行进一步的开发。
Asymmetric oxidation of sulfides by hydrogen peroxide catalyzed by chiral manganese porphyrins in water/methanol solution

作者：Hassan Srour、Joanna Jalkh、Paul Le Maux、Soizic Chevance、Marwan Kobeissi、Gérard Simonneaux

DOI：10.1016/j.molcata.2012.12.016

日期：2013.4

An efficient asymmetric oxidation of sulfides catalyzed by water-soluble chiral manganese porphyrin was carried out in presence of cheap and environmentally benign oxidant H2O2 at 25 °C. Prochiral sulfides were converted to respective sulfoxides with up to 100% conversion and up to 57% enantiomeric excess. The present study demonstrated the necessity of water as solvent and imidazole as co-catalyst

在廉价且对环境无害的氧化剂H 2 O 2的存在下，于25°C进行了水溶性手性锰卟啉催化的硫化物的有效不对称氧化。前手性硫化物转化为各自的亚砜，转化率最高为100％，对映体过量最高为57％。本研究表明水作为溶剂和咪唑作为助催化剂的必要性。证明了其在制备光学药物舒林酸中的应用。
Process for the preparation of organic compounds containing a sulfinyl or sulfonyl group

申请人：DINAMITE DIPHARMA S.P.A. abbreviated DIPHARMA S.P.A.

公开号：US20040192929A1

公开（公告）日：2004-09-30

A process for the oxidation of thioethers to sulfoxides or sulfones or for the oxidation of sulfoxides to sulfones by treatment of thioethers or sulfoxides with an oxidizing amount of &egr;-phthalimidoperhexanoic acid is particularly useful for the preparation of compounds of industrial interest, in particular pharmaceuticals for human or veterinary use.

一种将硫醚氧化为亚砜或砜，或将亚砜氧化为砜的过程，通过用适量的ε-邻苯二甲酰亚丙基己酸处理硫醚或亚砜，特别适用于制备工业感兴趣的化合物，特别是用于人类或兽医用途的药物。