4-(1,1-二甲基-2-丙炔基)-吗啉 | 7471-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: 4-(1,1-二甲基-2-丙炔基)-吗啉
• 英文名称: 4-(1,1-dimethylprop-2-ynyl)morpholine
• 英文别名: 4-(propyn-2-yl)morpholine；4-(1,1-dimethyl-prop-2-ynyl)-morpholine；3-Morpholino-3-methyl-butin-(1)；4-(2-Methylbut-3-yn-2-yl)morpholine
• CAS: 7471-07-0
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: BNRQMHZZZUFXNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-(1,1-二甲基-2-丙炔基)-吗啉 在 盐酸 、 氧气 、 氯化铵 、 copper(l) chloride 作用下， 生成 2,7-Dimorpholino-2,7-dimethyl-octadiin-(3,5)
  参考文献：
  名称：

  Oxidative Coupling and Cross-Coupling of Acetylenic Amines and Acetylenic Carbinols¹

  摘要：

  DOI：

  10.1021/jo01052a024
• 作为产物：
  描述：

  吗啉 、 3-氯-3-甲基-1-丁炔 在 三乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 4-(1,1-二甲基-2-丙炔基)-吗啉
  参考文献：
  名称：

  一种炔代喹啉衍生物及其制备方法和用途

  摘要：

  本发明公开了一种炔代喹啉衍生物及其制备方法和用途，所述的炔代喹啉衍生物为通式I所示的炔代喹啉类化合物及其药学上可接受的盐、水合物、溶剂化物、前药，它们的制备方法。本发明还是涉及通式I的化合物具有抑制多种蛋白酪氨酸激酶(例如c‑Met和VEGFR)活性，因此它们可用作抗癌药物，治疗人的癌症。

  公开号：

  CN104817497B

文献信息

• Quinazoline derivatives
  申请人：——

  公开号：US20040116422A1

  公开（公告）日：2004-06-17

  A compound of the formula (I) 1 or a pharmaceutically acceptable salt thereof, a hydrate thereof, a solvate thereof, an optically active compound thereof, a racemate thereof or a diastereomer mixture thereof has a superior tyrosine-specific protein kinase inhibitory activity and is useful as a pharmaceutical agent, particularly as an agent for the prophylaxis or treatment of various cancers, psoriasis or diseases caused by arteriosclerosis, and the like.

  式（I）的化合物或其药学上可接受的盐、水合物、溶剂合物、光学活性化合物、消旋体或其二对映异构体混合物具有优越的酪氨酸特异性蛋白激酶抑制活性，并且可用作药物剂，特别是作为各种癌症、银屑病或由动脉硬化引起的疾病的预防或治疗剂。
• Aminothiolester compounds, pharmaceutical and cosmetic compositions containing same and uses thereof
  申请人：——

  公开号：US20030181443A1

  公开（公告）日：2003-09-25

  The invention relates to novel aminothiol ester compounds having the general formula (I): 1 and to a method for preparing them and to their use in pharmaceutical compositions intended for use in human or veterinary medicine (cancers and precancers, dermatological, rheumatic and ophthalmological complaints in particular) or in cosmetic compositions. The invention also relates to a pharmaceutical or cosmetic composition, characterized in that it comprises, as active agent, a compound of general formula (I) in combination with a pharmaceutically or cosmetically acceptable support.

  该发明涉及一种具有通式(I)的新型氨基硫醇酯化合物，以及制备它们的方法，以及它们在制备用于人类或兽医学（尤其是癌症和癌前病变、皮肤病、风湿病和眼科疾病）的药物组合物或化妆品组合物中的使用。该发明还涉及一种药物或化妆品组合物，其特征在于它包含通式(I)的化合物作为活性剂，与药学或化妆品上可接受的载体相结合。
• Novel competitive irreversible inhibitors of aldehyde dehydrogenase (ALDH1): restoration of chemosensitivity of L1210 cells overexpressing ALDH1 and induction of apoptosis in BAF3 cells overexpressing bcl2
  作者：Gerard Quash、Guy Fournet、Jacqueline Chantepie、Jacques Gore、Claude Ardiet、Dominique Ardail、Yvonne Michal、Uwe Reichert

  DOI：10.1016/s0006-2952(02)01294-7

  日期：2002.10

  4-Amino-4-methyl-pent-2-ynthioc acid S-methyl ester (ampal thiolester: ATE) was used as a lead compound to synthesise new aminosubstituted derivatives of alpha,beta acetylenic thiolester compounds as inhibitors of aldehyde dehydrogenase 1, (ALDH1). Of these compounds, the dimethyl derivative (DIMATE) was a competitive irreversible inhibitor (K-i similar to 280 muM) of baker's yeast ALDH1 in vitro showing 80% inhibition at 400 muM when preincubated with the enzyme for 30 min, whereas the trimethyl ammonium and the morpholine derivatives showed only 15% inhibition at 600 muM even after 60 min preincubation. ATE inhibited ALDH1 activity in ALDH1-transfected L1210 T cells resistant to hydroperoxycyclophosphamide (HCPA) and inhibited growth synergistically in the presence of HCPA. In non-transfected L1210 counterparts ATE did not potentiate growth inhibition by HCPA. DIMATE was a 30-100-fold more effective growth inhibitor than ATE. Endogenous ALDH1 activities of BAF(3) cells over-expressing different levels of bcl(2) (0-100%) were similar (16-20 mU/mg protein) and were all inhibited by DIMATE, reaching 20-30% at 4 muM. Up to 4 muM no apoptosis, as measured by DNA-fragmentation was observed, but at 8 and 10 muM DIMATE, DNA-fragmentation increased concomitantly with ALDH1 inhibition. No DNA-fragmentation was observed with ALDH1 irreversible inhibitors devoid of a thiolester group or with thiolesters which were not inhibitors of ALDH1. It was seen only with competitive irreversible inhibitors having the methanethiol and enzyme-inhibitory moieties. The methanethiol putatively released from DIMATE by ALDH1 esterase activity plays a role, albeit undefined, in lowering intramitochondrial glutathione levels which decreased by 47% as DNA-fragmentation increased. (C) 2002 Elsevier Science Inc. All rights reserved.
• Aldehyde dehydrogenase inhibitors: α,β-Acetylenic N-substituted aminothiolesters are reversible growth inhibitors of normal epithelial but irreversible apoptogens for cancer epithelial cells from human prostate in culture
  作者：Gerard Quash、Guy Fournet、Charlotte Courvoisier、Rosa M. Martinez、Jacqueline Chantepie、Marie Julie Paret、Julie Pharaboz、Marie Odile Joly-Pharaboz、Jacques Goré、Jean André

  DOI：10.1016/j.ejmech.2007.06.004

  日期：2008.5

  The pharmacomodulation of the N atom of alpha,beta-acetylenic aminothiolesters or the replacement of the thiolester moiety by more electroplfflic groups did not permit any clear rationale to be established for improving the selective growth-inhibitory activity of this family of compounds over that of the previously synthesized alpha,beta-acetylenic aminothiolesters DIMATE and MATE [G. Quash, G. Fournet, J. Chantepie, J. Gore, C. Ardiet, D. Ardail, Y. Michal, U. Reichert, Biochem Phannacol 64 (2002) 1279-92]. Hence DIMATE and MATE were investigated more thoroughly for selectivity and growth-inhibitory activity using human prostate epithelial normal cells (HPENC) on the one hand and human prostate epithelial cancer cells (DU145) on the other. Unequivocal evidence was obtained showing that both compounds were reversible growth inhibitors of HPENC but irreversible growth inhibitors of DU145. Growth-inhibition of DU145 was due to the induction of early apoptosis as revealed by the flow cytometric analytical profile of inhibitor-treated cells, of the decrease in the redox potential and increase in superoxide anion content of their mitochondria. Of the two intracellular enzymes: aldehyde dehydrogenases 1 and 3 (ALDH1 and ALDH3) targeted by DIMATE and MATE, ALDH3 was inhibited to the same extent by both compounds whereas ALDH1 was less susceptible to inhibition by MATE. As the induction of ALDH3 by xenobiotics is hormone-dependent, MATE, the more selective of the two inhibitors, is a useful tool not only for examining the role of the ALDH3 isoform in hormone-sensitive and resistant prostate cancer cells in culture but also for investigating if it can inhibit the growth of xenografts of prostate cancer in immunodeficient mice. (C) 2007 Elsevier Masson SAS. All rights reserved.
• The Alkylation of Amines with t-Acetylenic Chlorides. Preparation of Sterically Hindered Amines¹
  作者：G. F. Hennion、Robert S. Hanzel

  DOI：10.1021/ja01503a040

  日期：1960.9