methyl (m-methoxyphenyl)carbodithioate | 37407-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl (m-methoxyphenyl)carbodithioate
• 英文别名: methyl 3-methoxybenzenecarbodithioate；3-methoxy-dithiobenzoic acid methyl ester
• CAS: 37407-45-7
• 化学式: C₉H₁₀OS₂
• 分子量: 198.31
• InChiKey: YYPKMZOKKBYHDL-UHFFFAOYSA-N

物化性质

• 沸点：
  307.3±44.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (m-methoxyphenyl)carbodithioate 在 sodium methylate 作用下， 以 水 为溶剂， 反应 33.25h， 生成 1-benzyl-4-hydroxy-3-(3-methoxy-phenyl)-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Use of a Pharmacophore Model for the Design of EGF-R Tyrosine Kinase Inhibitors:  4-(Phenylamino)pyrazolo[3,4-d]pyrimidines

  摘要：

  In the course of the random screening of a pool of CIBA chemicals, the two pyrazolopyrimidines 1 and 2 have been identified as fairly potent inhibitors of the EGF-R tyrosine kinase. Using a pharmacophore model for ATP-competitive inhibitors interacting with the active site of the EGF-R protein tyrosine kinase (PTK), the class of the pyrazolo[3,4-d]pyrimidines was then optimized in an interactive process leading to a series of 4-(phenylamino)-1H-pyrazolo[3,4-d]-pyrimidines as highly potent inhibitors of the EGF-R tyrosine kinase. The most potent compounds 13, 14, 15, 17, 19, 22, 26, 28, and 30 of this series inhibited the EGF-R PTK with IC50 values below 10 nM. High selectivity toward a panel of nonreceptor tyrosine kinases (c-Src, upsilon-Abl) and serine/threonine kinases (PKC alpha, CDK1) was observed. In cells, EGF-stimulated cellular tyrosine phosphorylation was inhibited by compounds 13, 15, 19, 22, and 23 at IC50 values below 50 nM, whereas PDGF-induced tyrosine phosphorylation was not affected by concentrations up to 10 mu M, thus indicating high selectivity for the inhibition of the ligand-activated EGF-R signal transduction pathway. Compounds 15 and 19 inhibited proliferation of the EGF-dependent MK cell line with IC50 values below 0.5 mu M. In addition, two compounds, 9 and 11, showing satisfactory oral bioavailability in mice after oral administration, exhibited good in vivo efficacy at doses of 12.5 and 50 mg/kg in a nude mouse tumor model using xenografts of the EGF-R overexpressing A431 cell line. From SAR studies, a binding mode for 4-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidines, especially for compound 15, at the ATP-binding site of the EGF-R tyrosine kinase is proposed. 4-(Phenylamino)-1H-pyrazolo[3,4-d]pyrimidines represent a new class of highly potent tyrosine kinase inhibitors which preferentially inhibit the EGF-mediated signal transduction pathway and have the potential for further evaluation as anticancer agents.

  DOI：

  10.1021/jm970124v
• 作为产物：
  描述：

  3-甲氧基苯甲醛 在 硫化氢 、 sulfur 作用下， 生成 methyl (m-methoxyphenyl)carbodithioate
  参考文献：
  名称：

  Drosten, Gisela; Mischke, Peter; Voss, Juergen, Chemische Berichte, 1987, vol. 120, p. 1757 - 1762

  摘要：

  DOI：

文献信息

• Pyrazole derivatives and processes for the preparation thereof
  申请人：Novartis AG

  公开号：US05981533A1

  公开（公告）日：1999-11-09

  4-Amino-1H-pyrazolo[3,4-d]pyrimidine derivatives of formula I ##STR1## wherein the symbols are as defined in claim 1, and intermediates for their manufacture are described. The compounds of formula I inhibit especially the tyrosine kinase activity of the receptor for epidermal growth factor and can be used, for example, in the case of epidermal hyperproliferation (psoriasis) and as anti-tumor agents.

  公式I的4-氨基-1H-吡唑并[3,4-d]嘧啶衍生物如下所示：其中符号如权利要求1中所定义，并描述了其制备的中间体。公式I的化合物特别抑制表皮生长因子受体的酪氨酸激酶活性，例如，在表皮过度增生（银屑病）和作为抗肿瘤剂中可以使用。
• Novel Route to 2,3-Substituted Benzo[<i>b</i>]thiophenes via Intramolecular Radical Cyclization
  作者：Prabal P. Singh、A. K. Yadav、H. Ila、H. Junjappa

  DOI：10.1021/jo900615p

  日期：2009.8.7

  A novel route to 2,3-substituted benzo[b]thiophenes by intramolecular radical cyclization of polarized ketene dithioacetals derived from o-bromoarylacetonitriles or the corresponding 3-(methylthio)-3-alkyl/aryl/heteroaryl analogues has been reported.

  已经报道了通过衍生自邻-溴芳基乙腈或相应的3-（甲硫基）-3-烷基/芳基/杂芳基类似物的极化的烯酮二硫缩醛的分子内自由基环化形成2，3-取代的苯并[ b ]噻吩的新途径。
• A NOVEL METHOD OF PREPARATION FOR ORTHOCARBOXYLATES FROM DITHIOCARBOXYLATES AND DIALKOXYDIBUTYLSTANNANES
  作者：Shizuyoshi Sakai、Tatsuo Fujinami、Kunio Kosugi、Kaoru Matsnaga

  DOI：10.1246/cl.1976.891

  日期：1976.8.5

  The reaction of methyl dithiocarboxylates with dialkoxydibutylstannanes at 60-95°C afforded the corresponding trialkyl orthocarboxylates in good yields.

  二硫代羧酸甲酯与二烷氧基二丁基锡烷在 60-95°C 的温度下反应，可以得到相应的三烷基原羧酸酯，收率很高。
• Tandem approach for the synthesis of 3-sulfenylimidazo[1,5-a]pyridines from dithioesters
  作者：Ajjahalli. B. Ramesha、Chottanahalli. S. Pavan Kumar、Nagarakere. C. Sandhya、Manikyanahalli. N. Kumara、Kempegowda Mantelingu、Kanchugarakoppal. S. Rangappa

  DOI：10.1039/c6ra03771b

  日期：——

  Iodine-mediated synthesis of 3-sulfenylimidazo[1,5-a]pyridines via C–H functionalization has been achieved using dithioesters, 2-methylaminopyridines and sulfonyl hydrazides. A library of 3-sulfanylimidazopyridines and imidazopyridines with broad functionalities are synthesized under metal-free reaction conditions.

  使用二硫酯，2-甲基氨基吡啶和磺酰肼，可以实现碘经C–H官能团介导的3-亚磺酰基咪唑并[1,5- a ]吡啶的合成。在无金属的反应条件下，合成了具有广泛功能的3-磺酰胺基咪唑并吡啶和咪唑并吡啶的文库。
• [EN] PYRAZOLE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF<br/>[FR] DERIVES DE PYRAZOLE ET LEURS PROCEDES DE PREPARATION
  申请人：NOVARTIS AG

  公开号：WO1996031510A1

  公开（公告）日：1996-10-10

  (EN) 4-Amino-1H-pyrazolo[3,4-d]pyrimidine derivatives of formula (I) wherein the symbols are as defined in claim (1), and intermediates for their manufacture are described. The compounds of formula (I) inhibit especially the tyrosine kinase activity of the receptor for epidermal growth factor and can be used, for example, in the case of epidermal hyperproliferation (psoriasis) and as anti-tumour agents.(FR) La présente invention décrit des dérivés de 4-amino-1H-pyrazolo[3,4-d]pyrimidine de formule (I), dans laquelle les symboles sont tels que définis dans la revendication (1), ainsi que les intermédiaires pour leur fabrication. Les composés de formule (I) inhibent tout particulièrement l'activité de tyrosine-kinase du récepteur du facteur de croissance épidermique et peuvent être utilisés, par exemple, dans le cas d'une hyperprolifération épidermique (psoriasis) et comme agents anti-tumoraux.

  本发明涉及4-氨基-1H-吡唑并吡啶衍生物，其通用化学式为(I)，其中各符号按权利要求1所定义。描述了相应的中间体，用于合成这些分子。分子的结构式为： 4-氨基-1H-吡唑并吡啶衍生物的通用化学式为： 这些化合物的表现特性可以在权利要求1中找到详尽解释。这些化合物可以通过特定的方法合成。它们的进步特性尤其是其对表皮生长因子受体的靶向抑制能力，这使得它们对治疗某些皮肤疾病（如光面性 enabled conditions，即银Haschick氏病（Psoriasis））以及某些癌症具有潜在的用途。