methyl 2-methylthiopyridine-3-carboxylate | 62658-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 2-methylthiopyridine-3-carboxylate
• 英文别名: methyl 2-(methylsulfanyl)nicotinate；methyl 2-(methylthio)nicotinate；2-methylsulfanylnicotinic acid methyl ester；Methyl 2-methylsulfanylpyridine-3-carboxylate
• CAS: 62658-91-7
• 化学式: C₈H₉NO₂S
• mdl: MFCD00661382
• 分子量: 183.231
• InChiKey: CIRMLVKTAPOENO-UHFFFAOYSA-N

物化性质

• 熔点：
  59.0-59.3 °C(Solv: hexane (110-54-3))
• 沸点：
  278.6±25.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-methylthiopyridine-3-carboxylate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (2-(甲基硫代)吡啶-3-基)甲醇
  参考文献：
  名称：

  Identification of MK-944a:  A Second Clinical Candidate from the Hydroxylaminepentanamide Isostere Series of HIV Protease Inhibitors

  摘要：

  Recent results from human clinical trials have established the critical role of HIV protease inhibitors in the treatment of acquired immune-deficiency syndrome (AIDS). However, the emergence of viral resistance, demanding treatment protocols, and adverse side effects have exposed the urgent need for a second generation of HIV protease inhibitors. The continued exploration of our hydroxylaminepentanamide (HAPA) transition-state isostere series of HIV protease inhibitors, which initially resulted in the identification of Crixivan (indinavir sulfate, MK-639, L-735,524), has now yielded MK-944a (L-756,423). This compound is potent, is selective, and competitively inhibits HIV-1 PR with a Ki value of 0.049 nM. It stops the spread of the HIVIIIb-infected MT4 lymphoid cells at 25.0-50.0 nM, even in the presence of alpha(1) acid glycoprotein, human serum albumin, normal human serum, or fetal bovine serum. MK-944a has a longer half-life in several animal models (rats, dogs, and monkeys) than indinavir sulfate and is currently in advanced human clinical trials.

  DOI：

  10.1021/jm9903848
• 作为产物：
  描述：

  甲醇 、 2-巯基烟酸 在 硫酸 作用下， 反应 8.0h， 以64%的产率得到methyl 2-methylthiopyridine-3-carboxylate
  参考文献：
  名称：

  S-Methylation of N-Containing Heterocyclic Thiols with Conjugated Acids of Methoxy Groups

  摘要：

  2-Mercaptopyridine-3-carboxylic acid reacts with methanol Under acidic conditions to afford the corresponding S-methylated methyl ester, methyl 2-methylthiopyridine-2-carboxylate. Such S-methylation Occurred for Various N-containing heterocyclic thiols with acidic methanol. The reaction proceeded by the attack of mercapto groups on the Conjugated acid of methanol. Therefore., the Sulfur atom of pyridine-2-thiol was also methylated with acidic methyl ethers or methyl esters.

  DOI：

  10.3987/com-09-11859

文献信息

• Synthesis and Antitumour Activity of New Derivatives of Flavone-8-acetic Acid (FAA). Part 31): 2-Heteroaryl Derivatives
  作者：R. Alan Aitken、Michael C. Bibby、Florian Bielefeldt、John A. Double、Andrea L. Laws、Anne-Laure Mathieu、Robert B. Ritchie、David W. J. Wilson

  DOI：10.1002/(sici)1521-4184(199812)331:12<405::aid-ardp405>3.0.co;2-2

  日期：1998.12

  A range of 14 derivatives of flavone‐8‐acetic acid (FAA) with a heterocyclic substituent in place of the 2‐phenyl group have been prepared and their anti‐tumour activity evaluated in vitro against a panel of human and murine tumour cell lines and in vivo against MAC 15A. Some of the compounds, notably 2c, d and s, showed significant in vivo activity and these require further studies in order to evaluate

  已经制备了一系列 14 种黄酮 - 8 - 乙酸 (FAA) 衍生物，其中杂环取代基取代了 2 - 苯基，并在体外针对一组人和鼠肿瘤细胞系评估了它们的抗肿瘤活性和在体内针对 MAC 15A。一些化合物，特别是 2c、d 和 s，显示出显着的体内活性，这些需要进一步研究以评估其发展潜力。
• [EN] INDOLE DERIVATIVES AS LIGANDS OF CRTH2 RECEPTORS<br/>[FR] DÉRIVÉS D'INDOLE EN TANT QUE LIGANDS DES RÉCEPTEURS CRTH2
  申请人：PULMAGEN THERAPEUTICS ASTHMA LTD

  公开号：WO2010142934A1

  公开（公告）日：2010-12-16

  The following compounds are CRTH2 antagonists, useful in treatment of respiratory disease: 3-[3-chloro-4-(pyridine-2-sulfonyl)isothiazol-5-ylmethyl]-5-fluoro-2- methylindol-1-yl}acetic acid, [3-(5-benzenesulfonyl-3-methyl-3H-imidazol-4-ylmethyl)-5-fluoro-2- methylindol-1-yl]acetic acid, [3-(5-benzenesulfonyloxazol-4-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid, [3-(3-benzenesulfonyl-4-met ylthiophen-2-ylmethyl)-5-fluoro-2-methylindol-1- yl]acetic acid, 5-fluoro-2-methyl-3-[2-(pyridin-2-ylsulfamoyl)benzyl]indol-1-yl}acetic acid, 5-fluoro-2-methyl-3-[4-methyl-3-(pyridine-2-sulfonyl)thiophen-2- ylmethyl]indol-1-yl}acetic acid, 5-fluoro-2-methyl-3-[3-methyl-5-(pyridine-2-sulfonyl)-3H-imidazol-4- ylmethyl]indol-1-yl}acetic acid, 5-fluoro-3-[2-(3-fluorophenylsulfamoyl)pyridin-3-ylmethyl]-2-methylindol-1- yl}acetic acid, [3-(4-benzenesulfonyloxazol-5-ylmethyl)-5-fluoro-2-methylindol-1- yl]acetic acid, 3-[2-(3-cyanophenylsulfamoyl)benzyl]-5-fluoro-2-methylindol-1-yl}acetic acid, [3-(4-benzenesulfonylthiazol-5-ylmethyl)-5-chloro-2-methyl-indol-1-yl]acetic acid, [3-(4-benzenesulfonyl-2-methylthiazol-5-ylmethyl)-5-fluoro-2-methylindol-1- yl]acetic acid, and [3-(4-benzenesulfonyl-3-methylisothiazol-5-ylmethyl)-5-fluoro-2- methylindol-1-yl]acetic acid.

  以下化合物是CRTH2拮抗剂，可用于治疗呼吸道疾病：3-[3-氯-4-(吡啶-2-磺酰基)异噻唑-5-基甲基]-5-氟-2-甲基吲哚-1-基}乙酸，[3-(5-苯磺酰基-3-甲基-3H-咪唑-4-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸，[3-(5-苯磺酰氧咪唑-4-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸，[3-(3-苯磺酰基-4-甲硫代吡啶-2-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸，5-氟-2-甲基-3-[2-(吡啶-2-基磺酰胺基)苯基]吲哚-1-基}乙酸，5-氟-2-甲基-3-[4-甲基-3-(吡啶-2-磺酰基)噻吩-2-基甲基]吲哚-1-基}乙酸，5-氟-2-甲基-3-[3-甲基-5-(吡啶-2-磺酰基)-3H-咪唑-4-基甲基]吲哚-1-基}乙酸，5-氟-3-[2-(3-氟苯基磺酰胺基)吡啶-3-基甲基]-2-甲基吲哚-1-基}乙酸，[3-(4-苯磺酰氧咪唑-5-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸，3-[2-(3-氰苯基磺酰胺基)苯基]-5-氟-2-甲基吲哚-1-基}乙酸，[3-(4-苯磺酰基噻唑-5-基甲基)-5-氯-2-甲基吲哚-1-基]乙酸，[3-(4-苯磺酰基-2-甲基噻唑-5-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸，和[3-(4-苯磺酰基-3-甲基异噻唑-5-基甲基)-5-氟-2-甲基吲哚-1-基]乙酸。
• Three 2-(methysulfanyl)nicotinamides
  作者：Ligia R. Gomes、John Nicolson Low、James L. Wardell、Alessandra C. Pinheiro、Thais C. N. de Mendonça、Marcus V. N. de Souza

  DOI：10.1107/s0108270113004344

  日期：2013.3.15

  The molecular conformations of threeN-alkyl-2-(methylsulfanyl)nicotinamide derivatives, namelyN-cyclohexyl-2-(methylsulfanyl)nicotinamide, C₁₃H₁₈N₂OS, (I),N-isopropyl-2-(methylsulfanyl)nicotinamide, C₁₀H₁₄N₂OS, (II), in which there are two molecules in the asymmetric unit which were chosen to form a hydrogen-bonded pair, andN-(2-hydroxyethyl)-2-(methylsulfanyl)nicotinamide dihydrate, C₉H₁₂N₂O₂S·2H₂O, (III), are compared with those of four unsubstitutedN-alkylnicotinamide compounds. The substituted compounds show a higher degree of torsion of the pyridine ring with respect to the amide group than do the unsubstituted compounds, with dihedral angles in the range 40–60° for the former and 20–35° for the latter. In (I) and (II), the supramolecular structure is defined by amide-N to carbonyl-O chains. In (III), the nicotinamide molecules are linked by hydrogen bonds to two water molecules resulting in two linked chains of rings which form the three-dimensional network.

  三种 N-烷基-2-(甲硫基)烟酰胺衍生物的分子构象，即 N-环己基-2-(甲硫基)烟酰胺，C13H18N2OS，(I)；N-异丙基-2-(甲硫基)烟酰胺，C10H14N2OS，(II)、以及 N-（2-羟乙基）-2-（甲硫基）烟酰胺二水合物 C9H12N2O2S-2H2O（III）与四种未取代的 N-烷基烟酰胺化合物进行了比较。与未取代的化合物相比，取代的化合物显示出吡啶环相对于酰胺基的扭转程度更高，前者的二面角在 40-60° 之间，后者的二面角在 20-35° 之间。在(I)和(II)中，超分子结构由酰胺-N 至羰基-O 链确定。在(III)中，烟酰胺分子通过氢键与两个水分子相连，形成两个相连的环链，构成三维网络。
• Cascade synthesis of new tetracyclic heteroaromatic thieno[2,3-b]pyridine-containing ring systems
  作者：R. Alan Aitken、Alasdair N. Garnett

  DOI：10.1039/b9nj00528e

  日期：——

  appropriate stabilised ylides, prepared in a few steps from 2-(methylthio)nicotinic acid, give products containing previously unknown naphtho-, phenanthro-, benzothieno- and benzofuro-fused thieno[2,3-b]pyridine ring systems.

  快速真空热解适当的稳定化的碘化物，可通过以下步骤制备 2-（甲硫基）烟酸，提供含有以前未知的萘，菲，苯并噻吩并和苯并呋喃稠合的产品 噻吩并[2,3- b ]吡啶 环系统。
• 2-（甲基磺酰基）烟醛的制备方法
  申请人：苏州源起材料科技有限公司

  公开号：CN116874418A

  公开（公告）日：2023-10-13

  本发明涉及2‑(甲基磺酰基)烟醛的制备方法，属于有机合成技术领域。本发明包括以下步骤：保护气氛下，将2‑巯基烟酸与碳酸钾溶于有机溶剂中，加入碘甲烷反应，得到白色固体2‑甲硫基烟酸甲酯；将所得2‑甲硫基烟酸甲酯与钨酸钠水合物溶于醋酸，在‑5℃～5℃的条件下加入氧化剂，室温反应，收集产物，得到白色固体2‑(甲基磺酰基)烟酸甲酯；保护气氛下，将所得2‑(甲基磺酰基)烟酸甲酯溶于四氢呋喃，在‑83℃～‑73℃的条件下加入还原剂搅拌反应，反应结束后，收集产物，得到2‑(甲基磺酰基)烟醛。本发明所得产物2‑(甲基磺酰基)烟醛的纯度为97％‑99％，总收率在70％以上。